Methanesulfonyl chloride → Tert-butyl 1-(4-chlorophenyl)-3-(methylsulfonamido)propylcarbamate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][CH:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Methanesulfonyl chloride (0.082 mL, 1.05 mmol) was added dropwise to tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamate (Intermediate 25) (300 mg, 1.05 mmol) and N,N-diisopropylethylamine (0.367 mL, 2.11 mmol) in DCM (4 mL) at 20° C. The resulting solution was stirred at 20° C. for 18 hours. The reaction mixture was concentrated and diluted with Et2O (25 mL) and washed with water (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in DCM. Pure fractions were evaporated to dryness to afford tert-butyl 1-(4-chlorophenyl)-3-(methylsulfonamido)propylcarbamate (275 mg, 71.9%) as a white solid.
Workup
- concentrationThe reaction mixture was concentrated
- additiondiluted with Et2O (25 mL)
- washwashed with water (25 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- customto afford crude product
- customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in DCM
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-21df19567c3142a1b552fbd80c89771c
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101623B2
Reaction notes
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