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

HRID 847624Notes

Reaction equation

HRID 847624 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-4983cd02aa3348f598f64fd60e9ce855
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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