3(R)-Benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran → 2(R)-Benzyl-9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide

HRID 863270Notes

Reaction equation

HRID 863270 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][C@@H:11]([C@@H:13]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:10][C:9]1=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(N)CCC>[CH2:13]([NH:28][C:9](=[O:36])[C@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:12][C@H:11]([OH:10])[C@@H:13]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:14][C:15]([CH3:26])([CH3:27])[CH2:16][CH2:17][O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:11][CH2:12][CH3:8]

Participants

3

Reactant 1

HCID 676254563(R)-Benzyl-5(S)-[5-benzyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxotetrahydrofuran

Product 1

HCID 867521032(R)-Benzyl-9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 502 mg of 3(R)-benzyl-5(S)-[5-benzyloxy-1 (S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran in 8.5 ml of butylamine is stirred at room temperature for 20 h and concentrated and the residue is purified by chromatography over silica gel (mobile phase A): Rf (A)=0.47; FAB-MS: (M+H)+ =569.

Workup

  1. concentrationconcentrated
  2. customthe residue is purified by chromatography over silica gel (mobile phase A)

Sources & evidence

ORD record
ord-1056d6f3352f4f399fa81d600552f34d
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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