Acetic Anhydride → 2-(Acetylamino)-4-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

HRID 1078125Notes

Reaction equation

HRID 1078125 reaction equation
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:3]([OH:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>ClCCl>[C:35]([NH:1][CH:2]([CH:3]([OH:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

Product 1

HCID 229102782-(Acetylamino)-4-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20 mg of the resultant compound of Example 11 and 0.05 ml of triethylamine in 1 ml of dichloromethane was cooled to 0° C. and treated with 0.01 ml of acetic anhydride. After 30 min, the solution was partitioned between water and dichloromethane, and the organic phase was dried over Na2SO4 and concentrated to give 23 mg (100%) of the desired compound (Rf 0.5, 10% methanol in chloroform). Mass spectrum: (M+H)+ =413.

Workup

  1. customthe solution was partitioned between water and dichloromethane
  2. dry with materialthe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-12f80abcf1bc473bbe6a846ddc5fcb7c
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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