Diisopropylamine → Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

HRID 2356042Notes

Reaction equation

HRID 2356042 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13]O)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(NC(C)C)(C)C.CS(Cl)(=O)=O.[C:28]1([SH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[C:9]([O:8][C:6]([NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:15])[CH2:13][S:34][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 7969ThiophenolHCID 31297Methanesulfonyl chlorideHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of N-(tert-butoxycarbonyl)-L-serine methyl ester (30 g, 137 mmol) and diisopropylamine (58 mL, 330 mmol) in dichloromethane (250 mL) was treated with methanesulfonyl chloride (11.65 mL, 151 mmol), stirred for 20 minutes, treated with thiophenol (15.5 mL, 151 mmol), warmed to room temperature, stirred for 30 minutes, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 310 (M−H)−.

Workup

  1. stirringstirred for 30 minutes
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a5ff2804f5fd4a29ae4e9cce05951abb
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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