Benzyl chloroformate → HCID 15380774, compound

HRID 1978054Notes

Reaction equation

HRID 1978054 reaction equation
ONC([C@H:5]([C@@H:15]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:16]([NH:18][N:19](S(C)(=O)=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[C:34](=[O:37])([O-:36])O.[Na+].Cl[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]>C(OCC)C>[C:9]([O:36][C:34]([C@H:5]([C@@H:15]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:16]([NH:18][N:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[O:17])[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:37])([CH3:14])([CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 15380763HCID 15380763, compound

Product 1

HCID 15380774HCID 15380774, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.5 g of 2(R)-[1(S)-(tert-butoxycarbonyl-4-phenylbutyl]-4-methyl-2′-phenylvalerohydrazide, prepared as described in Example 1, part (i), was dissolved in 10 ml of diethyl ether and stirred with 10 ml of saturated aqueous sodium hydrogen carbonate solution and 1.0 ml of benzyl chloroformate. After 24 hours the ether layer was separated, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulphate. After removal of the solvent the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (9.1) for the elution. There was obtained 0.767 g of benzyl 3-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleryl]-2-phenylcarbazate in the form of a white solid.

Workup

  1. customAfter 24 hours the ether layer was separated
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customAfter removal of the solvent the residue
  5. customwas purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-e507761eea244d5986468ef126029325
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

Loading…