Benzyl chloroformate → HCID 69129541, compound

HRID 1356213Notes

Reaction equation

HRID 1356213 reaction equation
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([NH:33][CH3:34])[CH:27]=2)[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:35]1[CH:40]=[CH:39][C:38]([CH2:41][O:42][C:43](Cl)=[O:44])=[CH:37][CH:36]=1>N1C=CC=CC=1>[CH2:41]([O:42][C:43](=[O:44])[N:33]([C:28]1[CH:27]=[C:26]([CH2:25][C@H:11]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:31]=[CH:30][C:29]=1[OH:32])[CH3:34])[C:38]1[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 69129234HCID 69129234, compound

Product 1

HCID 69129541HCID 69129541, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Crude (2S)-2-benzenesulfonylamino-3-(4-hydroxy-3-methylamino-phenyl)-N-(4-phenyl-butyl)-propionamide of Step A (170 mg, 0.35 mmol) is dissolved in pyridine (4 mL) and Cbz-Cl (60 μL, 0.40 mmol) is added at 0° C. The mixture is stirred at RT overnight. The solvent is removed by evaporation and the residue is dissolved in EtOAc and purified by column chromatography (hexane/EtOAc) to provide {5-[(2S)-2-benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-hydroxy-phenyl}-methyl-carbamic acid benzyl ester.

Workup

  1. customThe solvent is removed by evaporation
  2. dissolutionthe residue is dissolved in EtOAc
  3. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-89d064f6aedb42d7b25f6ba78f31111e
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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