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

HRID 2085710Notes

Reaction equation

HRID 2085710 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-191ae1181d0140ba85e8cded5542844f
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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