No renderable structure data available
COC(=O)C(C(=O)C1=CC=CC=C1)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2-amino-3-oxo-3-phenylpropanoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 54011-34-6 |
| Database ID | 13290648 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2-amino-3-oxo-3-phenylpropanoate (CAS 54011-34-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 13290648
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0247fd9b71804ce0a61d48d5a23e0893Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid (5.49 g; 17.42 mmol) was dissolved in dry tetrahydrofuran (200 ml) and N-methylmorpholine (1.92 ml; 17.42 mmol) was added. The reaction mixture was cooled to -20° C. and stirred 15 min. Isobutyl chloroformate (2.27 ml; 17.42 mmol) was dissolved in dry tetrahydrofuran (3 ml) and added dropwise to the reaction mixture at -20° C. N-methylmorpholine (1.92 ml; 17.42 mmol) and 2-amino-3-oxo-3-phenylpropionic acid methylester (4.0 g; 17.42 mmol) were added and and the mixture was stirred 30 min at -20° C. The reaction mixture was heated to room temperature and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (200 ml), washed with water (200 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (5×45 cm) using heptane/ethyl acetate/methylene chloride (2:1:1) as eluent to afford 6.19 g of a diastereomeric mixture of 2-((2R)-2-tert-butoxycarbonylamino-3-(2-naphthyl)propionylamino)-3-oxo-3-phenylpropionic acid methylester. added dropwise to the reaction mixture at -20° C the mixture was stirred 30 min at -20° C The reaction mixture was heated to room temperature the solvent was removed in vacuo The residue was dissolved in methylene chloride (200 ml) washed with water (200 ml) dried (magnesium sulfate) The solvent was removed in vacuo the residue was chromatographed on silica (5×45 cm)
Source ID: ord-1493aa39239c45f88b189767790982d5Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid (5.49 g; 17.42 mmol) was dissolved in dry tetrahydrofuran (200 ml) and N-methylmorpholine (1.92 ml; 17.42 mmol) was added. The reaction mixture was cooled to -20° C. and stirred 15 min. Isobutyl chloroformate (2.27 ml; 17.42 mmol) was dissolved in dry tetrahydrofuran (3 ml) and added dropwise to the reaction mixture at -20° C. N-methylmorpholine (1.92 ml; 17.42 mmol) and 2-amino-3-oxo-3-phenylpropionic acid methylester (4.0 g; 17.42 mmol) were added and and the mixture was stirred 30 min at -20° C. The reaction mixture was heated to room temperature and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (200 ml), washed with water (200 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (5×45 cm) using heptane/ethyl acetate/methylene chloride (2:1:1) as eluent to afford 6.19 g of a diastereomeric mixture of 2-((2R)-2-tert-butoxycarbonylamino-3-(2-naphthyl)propionylamino)-3-oxo-3-phenylpropionic acid methylester. added dropwise to the reaction mixture at -20° C the mixture was stirred 30 min at -20° C The reaction mixture was heated to room temperature the solvent was removed in vacuo The residue was dissolved in methylene chloride (200 ml) washed with water (200 ml) dried (magnesium sulfate) The solvent was removed in vacuo the residue was chromatographed on silica (5×45 cm)
Source ID: ord-1493aa39239c45f88b189767790982d5Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dry tetrahydrofuran (250 ml) was cooled to -78° C. Potassium tert-butoxide (6.37 g; 56.72 mmol) was dissolved in dry tetrahydrofuran (100 ml) and added. (Benzhydrylideneamino)acetic acid methyl ester (14.35 g; 56.72 mmol) was added and the reaction mixture was stirred 30 min at -78° C. Benzoyl chloride (6.59 g; 56.72 mmol) was added dropwise and the reaction mixture was stirred 30 min at -78° C. Hydrochloric acid (1.0 M; 175 ml) was added dropwise. The reaction mixture was heated to room temperature and 2/3 of the solvent was removed in vacuo. Water (700 ml) was added and the reaction mixture was washed with diethyl ether (400 ml). The aqueous phase was evaporated in vacuo and the residue was dissolved in methanol and evaporated (2×150 ml). Methanol (80 ml) was added. The mixture was filtrated and the filtrate was evaporated in vacuo. The residue was recrystallised from tetrahydrofuran/diethyl ether to afford 8.86 g of 2-amino-3-oxo-3-phenylpropionic acid methylester as a hydrochloride. added the reaction mixture was stirred 30 min at -78° C The reaction mixture was heated to room temperature 2/3 of the solvent was removed in vacuo Water (700 ml) was added the reaction mixture was washed with diethyl ether (400 ml) The aqueous phase was evaporated in vacuo the residue was dissolved in methanol evaporated (2×150 ml) Methanol (80 ml) was added The mixture was filtrated the filtrate was evaporated in vacuo The residue was recrystallised from tetrahydrofuran/diethyl ether
Source ID: ord-1a33de8d65b34484873978489d505875Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid (5.49 g; 17.42 mmol) was dissolved in dry tetrahydrofuran (200 ml) and N-methylmorpholine (1.92 ml; 17.42 mmol) was added. The reaction mixture was cooled to −20° C. and stirred 15 min. Isobutyl chloroformate (2.27 ml; 17.42 mmol) was dissolved in dry tetrahydrofuran (3 ml) and added dropwise to the reaction mixture at −20° C. N-methylmorpholine (1.92 ml; 17.42 mmol) and 2-amino-3-oxo-3-phenylpropionic acid methylester (4.0 g; 17.42 mmol) were added and and the mixture was stirred 30 min at −20° C. The reaction mixture was heated to room temperature and the solvent was. removed in vacuo. The residue was dissolved in methylene chloride (200 ml), washed with water (200 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (5×45 cm) using heptane/ethyl acetate/methylene chloride (2:1:1) as eluent to afford 6.19 g of a diastereomeric mixture of 2-((2R)-2-tert-butoxycarbonylamino-3-(2-naphthyl)propionylamino)-3-oxo-3-phenylpropionic acid methylester. added dropwise to the reaction mixture at −20° C the mixture was stirred 30 min at −20° C The reaction mixture was heated to room temperature removed in vacuo The residue was dissolved in methylene chloride (200 ml) washed with water (200 ml) dried (magnesium sulfate) The solvent was removed in vacuo the residue was chromatographed on silica (5×45 cm)
Source ID: ord-639e18bb5b984dada19aa7a4cc3a8ea6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dry tetrahydrofuran (250 ml) was cooled to −78° C. Potassium tert-butoxide (6.37 g; 56.72 mmol) was dissolved in dry tetrahydrofuran (100 ml) and added. (Benzhydrylideneamino) acetic acid methyl ester (14.35 g; 56.72 mmol) was added and the reaction mixture was stirred 30 min at −78° C. Benzoyl chloride (6.59 g; 56.72 mmol) was added dropwise and the reaction mixture was stirred 30 min at −78° C. Hydrochloric acid (1.0 M; 175 ml) was added dropwise. The reaction mixture was heated to room temperature and 2/3 of the solvent was removed in vacuo. Water (700 ml) was added and the reaction mixture was washed with diethyl ether (400 ml). The aqueous phase was evaporated in vacuo and the residue was dissolved in methanol and evaporated (2×150 ml). Methanol (80 ml) was added. The mixture was filtrated and the filtrate was evaporated in vacuo. The residue was recrystallised from tetrahydrofuran/diethyl ether to afford 8.86 g of 2-amino-3-oxo-3-phenylpropionic acid methylester as a hydrochloride. added the reaction mixture was stirred 30 min at −78° C The reaction mixture was heated to room temperature 2/3 of the solvent was removed in vacuo Water (700 ml) was added the reaction mixture was washed with diethyl ether (400 ml) The aqueous phase was evaporated in vacuo the residue was dissolved in methanol evaporated (2×150 ml) Methanol (80 ml) was added The mixture was filtrated the filtrate was evaporated in vacuo The residue was recrystallised from tetrahydrofuran/diethyl ether
Source ID: ord-ebf9ceb1d0964200b767543c0e77c089Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid (5.49 g; 17.42 mmol) was dissolved in dry tetrahydrofuran (200 ml) and N-methylmorpholine (1.92 ml; 17.42 mmol) was added. The reaction mixture was cooled to -20° C. and stirred 15 min. Isobutyl chloroformate (2.27 ml; 17.42 mmol) was dissolved in dry tetrahydrofuran (3 ml) and added dropwise to the reaction mixture at -20° C. N-methylmorpholine (1.92 ml; 17.42 mmol) and 2-amino-3-oxo-3-phenylpropionic acid methylester (4.0 g; 17.42 mmol) were added and and the mixture was stirred 30 min at -20° C. The reaction mixture was heated to room temperature and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (200 ml), washed with water (200 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (5×45 cm) using heptane/ethyl acetate/methylene chloride (2:1:1) as eluent to afford 6.19 g of a diastereomeric mixture of 2-((2R)-2-tert-butoxycarbonylamino-3-(2-naphthyl)propionylamino)-3-oxo-3-phenylpropionic acid methylester. added dropwise to the reaction mixture at -20° C the mixture was stirred 30 min at -20° C The reaction mixture was heated to room temperature the solvent was removed in vacuo The residue was dissolved in methylene chloride (200 ml) washed with water (200 ml) dried (magnesium sulfate) The solvent was removed in vacuo the residue was chromatographed on silica (5×45 cm)
Source ID: ord-1493aa39239c45f88b189767790982d5Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dry tetrahydrofuran (250 ml) was cooled to -78° C. Potassium tert-butoxide (6.37 g; 56.72 mmol) was dissolved in dry tetrahydrofuran (100 ml) and added. (Benzhydrylideneamino)acetic acid methyl ester (14.35 g; 56.72 mmol) was added and the reaction mixture was stirred 30 min at -78° C. Benzoyl chloride (6.59 g; 56.72 mmol) was added dropwise and the reaction mixture was stirred 30 min at -78° C. Hydrochloric acid (1.0 M; 175 ml) was added dropwise. The reaction mixture was heated to room temperature and 2/3 of the solvent was removed in vacuo. Water (700 ml) was added and the reaction mixture was washed with diethyl ether (400 ml). The aqueous phase was evaporated in vacuo and the residue was dissolved in methanol and evaporated (2×150 ml). Methanol (80 ml) was added. The mixture was filtrated and the filtrate was evaporated in vacuo. The residue was recrystallised from tetrahydrofuran/diethyl ether to afford 8.86 g of 2-amino-3-oxo-3-phenylpropionic acid methylester as a hydrochloride. added the reaction mixture was stirred 30 min at -78° C The reaction mixture was heated to room temperature 2/3 of the solvent was removed in vacuo Water (700 ml) was added the reaction mixture was washed with diethyl ether (400 ml) The aqueous phase was evaporated in vacuo the residue was dissolved in methanol evaporated (2×150 ml) Methanol (80 ml) was added The mixture was filtrated the filtrate was evaporated in vacuo The residue was recrystallised from tetrahydrofuran/diethyl ether
Source ID: ord-1a33de8d65b34484873978489d505875PubChem References
These sources are listed in the compound's public database record.
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