No renderable structure data available
CCOC(=O)NS(=O)(=O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl N-methylsulfonylcarbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 49671-33-2 |
| Database ID | 1201508 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl N-methylsulfonylcarbamate (CAS 49671-33-2) 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 1201508
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-f040360508f34342ad528c43cdc7fef8Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of compound 10b (82 mg, 0.18 mmol) and compound 12a (0.14 g, 0.86 mmol) in DMF (2 mL) was added DIEA (0.16 mL, 0.91 mmol). The mixture was stirred at 100° C. for 2 h. The solution was cooled down, and diluted with DCM (10 mL). The organic layer was washed with 1 N HCl solution (10 mL) and brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash column chromatography on silica gel (0-10% CH3OH/DCM) to give the title compound 50 as a red solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.96 (s, 1H), 8.31 (d, J=8.6 Hz, 1H), 8.12 (d, J=5.6 Hz, 1H), 7.94 (dd, J=13.6, 8.2 Hz, 2H), 7.83 (d, J=8.6 Hz, 1H), 7.66-7.77 (m, 5H), 7.57-7.63 (m, 2H), 7.51-7.57 (m, 1H), 6.40 (d, J=5.9 Hz, 1H), 4.03-4.14 (m, 4H), 3.83-3.92 (m, 4H), 3.17 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H27N7O4S: 570.2 (M+H). Found 570.4. The solution was cooled down The organic layer was washed with 1 N HCl solution (10 mL) and brine dried over MgSO4 filtered concentrated The resulting residue was purified by flash column chromatography on silica gel (0-10% CH3OH/DCM)
Source ID: ord-eca9fddd513c4d499d5fd4a61e153d05Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of methanesulfonamide (1.0 g, 11 mmol), triethylamine (1.9 mL, 14 mmol), and DMAP (0.13 g, 1.1 mmol) in DCM (20 mL) cooled in an ice-water bath was added ethyl carbonochloridate (1.1 mL, 12 mmol) dropwise via a syringe under an argon atmosphere. The mixture was allowed to warm up to rt overnight. The reaction mixture was concentrated, and the residue obtained was dissolved in EtOAc (100 mL). The solution was washed with 1 N HCl (20 mL) and brine, and dried over MgSO4. The mixture was filtered and concentrated to give compound 12a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.86 (br. s., 1H), 4.28 (q, J=7.25 Hz, 2H), 3.30 (s, 3H), 1.33 (t, J=7.25 Hz, 3H). cooled in an ice-water bath The reaction mixture was concentrated the residue obtained The solution was washed with 1 N HCl (20 mL) and brine dried over MgSO4 The mixture was filtered concentrated
Source ID: ord-8f0d9d82708642078e53390089a88bccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of methanesulfonamide (1.0 g, 11 mmol), triethylamine (1.9 mL, 14 mmol), and DMAP (0.13 g, 1.1 mmol) in DCM (20 mL) cooled in an ice-water bath was added ethyl carbonochloridate (1.1 mL, 12 mmol) dropwise via a syringe under an argon atmosphere. The mixture was allowed to warm up to rt overnight. The reaction mixture was concentrated, and the residue obtained was dissolved in EtOAc (100 mL). The solution was washed with 1 N HCl (20 mL) and brine, and dried over MgSO4. The mixture was filtered and concentrated to give compound 12a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.86 (br. s., 1H), 4.28 (q, J=7.25 Hz, 2H), 3.30 (s, 3H), 1.33 (t, J=7.25 Hz, 3H). cooled in an ice-water bath The reaction mixture was concentrated the residue obtained The solution was washed with 1 N HCl (20 mL) and brine dried over MgSO4 The mixture was filtered concentrated
Source ID: ord-8f0d9d82708642078e53390089a88bccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f040360508f34342ad528c43cdc7fef8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-[2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide (Example 31) (0.15 g) and (methylsulfonyl)-carbamic acid ethyl ester (0.065 g) were heated with a single mode microwave in a sealed 10 mL vial for 30 minutes at 130° C. The residue was purified on a Varian® NH2 cartridge washed with methanol (50 mL) and eluted with acetic acid:methanol (10:90) to afford the title product (0.016 g). The residue was purified on a Varian® NH2 cartridge washed with methanol (50 mL) eluted with acetic acid:methanol (10:90)
Source ID: ord-f396b0db1e3a490b99b7d01917cf3561Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-[2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide (Example 31) (0.15 g) and (methylsulfonyl)-carbamic acid ethyl ester (0.065 g) were heated with a single mode microwave in a sealed 10 mL vial for 30 minutes at 130° C. The residue was purified on a Varian® NH2 cartridge washed with methanol (50 mL) and eluted with acetic acid:methanol (10:90) to afford the title product (0.016 g). The residue was purified on a Varian® NH2 cartridge washed with methanol (50 mL) eluted with acetic acid:methanol (10:90)
Source ID: ord-f396b0db1e3a490b99b7d01917cf3561Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of compound 59a (100 mg, 0.147 mmol) and ethyl methylsulfonylcarbamate (148 mg, 0.888 mmol) and DIEA (0.191 mL, 1.11 mmol) in DMF (2 mL) was stirred at 100° C. for 2 h. The reaction mixture was allowed to cool to rt and diluted with DCM. The reaction mixture was concentrated and the residue obtained was purified by flash column chromatography on silica gel (0-20% MeOH/EtOAc), recrystallized with EtOAc/heptanes and purified by prep-TLC (1:5:5 MeOH/DCM/EtOAc) to give the title compound 40. 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.22-3.30 (m, 2H), 3.33 (s, 3H), 3.37-3.47 (m, 2H), 3.69-3.87 (m, 4H), 4.03-4.21 (m, 4H), 7.16 (s, 1H), 7.31 (s, 1H), 7.28 (s, 1H), 7.39 (d, J=8.3 Hz, 1H), 7.43-7.60 (m, 3H), 7.67-7.76 (m, 1H), 7.82 (d, J=7.6 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 8.15 (d, J=8.3 Hz, 1H), 8.81 (br. s., 1H). Mass Spectrum LCMS, ESI (pos.) Calcd. for C29H29N7O4S: 572.2 [M+H]. found 572.5. to cool to rt The reaction mixture was concentrated the residue obtained was purified by flash column chromatography on silica gel (0-20% MeOH/EtOAc) recrystallized with EtOAc/heptanes purified by prep-TLC (1:5:5 MeOH/DCM/EtOAc)
Source ID: ord-93b83ec492ef4d5ab664e5a48677f2dfConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of compound 10b (82 mg, 0.18 mmol) and compound 12a (0.14 g, 0.86 mmol) in DMF (2 mL) was added DIEA (0.16 mL, 0.91 mmol). The mixture was stirred at 100° C. for 2 h. The solution was cooled down, and diluted with DCM (10 mL). The organic layer was washed with 1 N HCl solution (10 mL) and brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash column chromatography on silica gel (0-10% CH3OH/DCM) to give the title compound 50 as a red solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.96 (s, 1H), 8.31 (d, J=8.6 Hz, 1H), 8.12 (d, J=5.6 Hz, 1H), 7.94 (dd, J=13.6, 8.2 Hz, 2H), 7.83 (d, J=8.6 Hz, 1H), 7.66-7.77 (m, 5H), 7.57-7.63 (m, 2H), 7.51-7.57 (m, 1H), 6.40 (d, J=5.9 Hz, 1H), 4.03-4.14 (m, 4H), 3.83-3.92 (m, 4H), 3.17 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H27N7O4S: 570.2 (M+H). Found 570.4. The solution was cooled down The organic layer was washed with 1 N HCl solution (10 mL) and brine dried over MgSO4 filtered concentrated The resulting residue was purified by flash column chromatography on silica gel (0-10% CH3OH/DCM)
Source ID: ord-eca9fddd513c4d499d5fd4a61e153d05Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of methanesulfonamide (1.0 g, 11 mmol), triethylamine (1.9 mL, 14 mmol), and DMAP (0.13 g, 1.1 mmol) in DCM (20 mL) cooled in an ice-water bath was added ethyl carbonochloridate (1.1 mL, 12 mmol) dropwise via a syringe under an argon atmosphere. The mixture was allowed to warm up to rt overnight. The reaction mixture was concentrated, and the residue obtained was dissolved in EtOAc (100 mL). The solution was washed with 1 N HCl (20 mL) and brine, and dried over MgSO4. The mixture was filtered and concentrated to give compound 12a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.86 (br. s., 1H), 4.28 (q, J=7.25 Hz, 2H), 3.30 (s, 3H), 1.33 (t, J=7.25 Hz, 3H). cooled in an ice-water bath The reaction mixture was concentrated the residue obtained The solution was washed with 1 N HCl (20 mL) and brine dried over MgSO4 The mixture was filtered concentrated
Source ID: ord-8f0d9d82708642078e53390089a88bccPubChem References
These sources are listed in the compound's public database record.
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