Benzyl chloroformate → HCID 54326145, compound

HRID 1432900Notes

Reaction equation

HRID 1432900 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:36])[CH2:15][NH:16][CH2:17][CH:18]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:36])[CH2:15][N:16]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:17][CH:18]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 54233772HCID 54233772, compound

Product 1

HCID 54326145HCID 54326145, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylchloroformate (1.4 mL, 9.81 mmol) is added dropwise to a solution of N,N-dimethylaminopyridine (1.09 g, 8.93 mmol) and [2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propylamino]-acetic acid methyl ester (3.06 g, 8.12 mmol) in CH2Cl2 at RT. The resulting mixture is stirred overnight then concentrated to dryness. The crude product is purifed by flash chromatography eluting with 1% MeOH/CH2Cl2 to yield the title compound (3.52 g, 6.89 mmol) as a colorless oil. Ion spray MS, [M+H]+=511.

Workup

  1. concentrationthen concentrated to dryness
  2. washeluting with 1% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-11ad8517955a4710a844420888b89083
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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