Triethylamine → Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate
Reaction equation
[C:1]([O:5][C:6](=[O:15])[CH:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[CH:7]([NH:14][S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Procedure
To a stirred solution of tert-butyl-2-amino-2-phenylacetate (1.34 g, 6.45 mmol) and methyl 3-(chlorosulfonyl)benzoate (1.53 g, 6.51 mmol) in tetrahydrofuran (15 mL) was added triethylamine (0.90 mL, 6.45 mmol) in one portion at ambient temperature. The reaction mixture was stirred for 30 minutes, after which time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL). The resulting organic phases were dried over magnesium sulfate and concentrated under reduced pressure to yield a crude solid. The solid was triturated in diethyl ether (5 mL) and cold methanol (5 mL) to yield the title compound as a white solid (1.13 g, 43%).
Workup
- concentrationafter which time, the reaction mixture was concentrated under reduced pressure
- custompartitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL)
- dry with materialThe resulting organic phases were dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto yield a crude solid
- customThe solid was triturated in diethyl ether (5 mL)
Sources & evidence
- ORD record
- ord-7d85209e3f1244728aa3851869eca2c7
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090606B2
Reaction notes
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