Benzyl chloroformate → 2-(t-Butyloxycarbonyl)amino-4S-hydroxy-5S-(benzyloxycarbonyl)amino-1,6-diphenyl-2-azahexane

HRID 1291783Notes

Reaction equation

HRID 1291783 reaction equation
[OH:1][C@H:2]([C@@H:20]([NH2:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C([O-])([O-])=O.[K+].[K+].[CH2:35]([O:42][C:43](Cl)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.OS([O-])(=O)=O.[K+]>O1CCOCC1.O>[OH:1][C@H:2]([C@@H:20]([NH:28][C:43]([O:42][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:44])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 186598251-[2(S)-Hydroxy-3(S)-amino-4-phenyl-butyl]-1-[phenylmethyl]-2-[tert-butoxycarbonyl]-hydrazine

Product 1

HCID 4647592-(t-Butyloxycarbonyl)amino-4S-hydroxy-5S-(benzyloxycarbonyl)amino-1,6-diphenyl-2-azahexane

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Under a nitrogen atmosphere, 220 mg (0.57 mmol) of 1-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[phenylmethyl]-2-[tert-butoxycarbonyl]-hydrazine (=H-[PheNNPhe]-Boc, Example 30b) in 15 ml of dioxane/water 1:1 and 408 mg (2.9 mmol) of K2CO3 are reacted with 120 mg (0.69 mmol) of chloroformic acid benzyl ester for 16 h at RT. KHSO4 solution is added, the mixture is extracted with 3 portions of ethyl acetate, and the organic phases are washed with water and brine, dried with Na2SO4 and concentrated by evaporation. Digestion from hexane yields the pure title compound: TLC Rf (I)=0.52; tRet (V)=17.1 min; FAB-MS (M+H)+ =520.

Workup

  1. extractionthe mixture is extracted with 3 portions of ethyl acetate
  2. washthe organic phases are washed with water and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-33ea223fa5a24d9999e9d9ba474ef9c0
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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