No renderable structure data available
CC(OC(NC(C(OCC1C=CC=CC=1)=O)CO)=O)(C)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | BENZYL N-(TERT-BUTOXYCARBONYL)SERINATE |
|---|---|
| IUPAC Name | — |
| CAS Number | 145612-59-5 |
| Database ID | 12953535 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
BENZYL N-(TERT-BUTOXYCARBONYL)SERINATE (CAS 145612-59-5) 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 12953535
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1387ff8fb4724cc3b9c5879d46159330Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c13c37e18bb54dcbb8655b75bfa872d9Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester (29.5 g) in dichloromethane (300 ml), triethylamine (21 ml) and mesyl chloride (8.6 ml) were added and the reaction solution was stirred for 30 minutes at 4° C. The reaction solution was added to 1 N hydrochloric acid cooling with ice. The obtained yellow oil was dissolved into dichloromethane (300 ml), and diisopropylethylamine (17 ml) and 4-methoxybenzenethiol (12 ml) were added thereto at 4° C. and the reaction solution was stirred for 3 hours at room temperature and concentrated. The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (24.8 g) having the following physical data. were added at 4° C. and the reaction solution was stirred for 3 hours at room temperature concentrated The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1)
Source ID: ord-e60addf815e34a8d82b9412f22d8d2bfConditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester (29.5 g) in dichloromethane (300 ml), triethylamine (21 ml) and mesyl chloride (8.6 ml) were added and the reaction solution was stirred for 30 minutes at 4° C. The reaction solution was added to 1 N hydrochloric acid cooling with ice. The obtained yellow oil was dissolved into dichloromethane (300 ml), and diisopropylethylamine (17 ml) and 4-methoxybenzenethiol (12 ml) were added thereto at 4° C. and the reaction solution was stirred for 3 hours at room temperature and concentrated. The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (24.8 g) having the following physical data. were added at 4° C. and the reaction solution was stirred for 3 hours at room temperature concentrated The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1)
Source ID: ord-e60addf815e34a8d82b9412f22d8d2bfConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of the compound of Formula XII(a), benzyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate (1 g, 3.38 mmol) in acetonitrile (10 mL) was added copper(I) iodide (64.4 mg, 0.338 mmol) and sodium sulfate (48.1 mg, 0.338 mmol). The resulting mixture was stirred at 60° C. and treated with 2,2-difluoro-2-fluorosulfonylacetic acid (524 μL, 5.08 mmol), dropwise, as a solution in acetonitrile (2 mL) over a period of 1.5 h. Upon completion of the addition, the mixture was stirred for a further 30 min then cooled to room temperature. The mixture was diluted with diethyl ether and washed with brine (2×), water (3×) and brine (1×). The organic phase was dried, filtered and concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes, to provide the compound of Formula XIII(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester (458 mg, 40%) as a colorless sticky oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.32-7.38 (m, 5H), 6.18 (wt, 1H), 5.28 (dd, 1H), 5.19 (dd, 2H), 4.55 (dt, 1H) 4.22 (td, 1H), 4.15 (m, 2H), 1.38 (s, 9H). Upon completion of the addition the mixture was stirred for a further 30 min then cooled to room temperature washed with brine (2×), water (3×) and brine (1×) The organic phase was dried filtered concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes
Source ID: ord-fdbbf23e8ab34ac6a6515ce0bc08c2cdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1387ff8fb4724cc3b9c5879d46159330Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of the compound of Formula XII(a), benzyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate (1 g, 3.38 mmol) in acetonitrile (10 mL) was added copper(I) iodide (64.4 mg, 0.338 mmol) and sodium sulfate (48.1 mg, 0.338 mmol). The resulting mixture was stirred at 60° C. and treated with 2,2-difluoro-2-fluorosulfonylacetic acid (524 μL, 5.08 mmol), dropwise, as a solution in acetonitrile (2 mL) over a period of 1.5 h. Upon completion of the addition, the mixture was stirred for a further 30 min then cooled to room temperature. The mixture was diluted with diethyl ether and washed with brine (2×), water (3×) and brine (1×). The organic phase was dried, filtered and concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes, to provide the compound of Formula XIII(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester (458 mg, 40%) as a colorless sticky oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.32-7.38 (m, 5H), 6.18 (wt, 1H), 5.28 (dd, 1H), 5.19 (dd, 2H), 4.55 (dt, 1H) 4.22 (td, 1H), 4.15 (m, 2H), 1.38 (s, 9H). Upon completion of the addition the mixture was stirred for a further 30 min then cooled to room temperature washed with brine (2×), water (3×) and brine (1×) The organic phase was dried filtered concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes
Source ID: ord-fdbbf23e8ab34ac6a6515ce0bc08c2cdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c13c37e18bb54dcbb8655b75bfa872d9Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester (29.5 g) in dichloromethane (300 ml), triethylamine (21 ml) and mesyl chloride (8.6 ml) were added and the reaction solution was stirred for 30 minutes at 4° C. The reaction solution was added to 1 N hydrochloric acid cooling with ice. The obtained yellow oil was dissolved into dichloromethane (300 ml), and diisopropylethylamine (17 ml) and 4-methoxybenzenethiol (12 ml) were added thereto at 4° C. and the reaction solution was stirred for 3 hours at room temperature and concentrated. The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (24.8 g) having the following physical data. were added at 4° C. and the reaction solution was stirred for 3 hours at room temperature concentrated The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1)
Source ID: ord-e60addf815e34a8d82b9412f22d8d2bfConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of the compound of Formula XII(a), benzyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate (1 g, 3.38 mmol) in acetonitrile (10 mL) was added copper(I) iodide (64.4 mg, 0.338 mmol) and sodium sulfate (48.1 mg, 0.338 mmol). The resulting mixture was stirred at 60° C. and treated with 2,2-difluoro-2-fluorosulfonylacetic acid (524 μL, 5.08 mmol), dropwise, as a solution in acetonitrile (2 mL) over a period of 1.5 h. Upon completion of the addition, the mixture was stirred for a further 30 min then cooled to room temperature. The mixture was diluted with diethyl ether and washed with brine (2×), water (3×) and brine (1×). The organic phase was dried, filtered and concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes, to provide the compound of Formula XIII(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester (458 mg, 40%) as a colorless sticky oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.32-7.38 (m, 5H), 6.18 (wt, 1H), 5.28 (dd, 1H), 5.19 (dd, 2H), 4.55 (dt, 1H) 4.22 (td, 1H), 4.15 (m, 2H), 1.38 (s, 9H). Upon completion of the addition the mixture was stirred for a further 30 min then cooled to room temperature washed with brine (2×), water (3×) and brine (1×) The organic phase was dried filtered concentrated in vacuo then chromatographed in 0-30% ethyl acetate in hexanes
Source ID: ord-fdbbf23e8ab34ac6a6515ce0bc08c2cdPubChem References
These sources are listed in the compound's public database record.
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