L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → Boc-Leu-Gly-Leu-Ala-OBzl

HRID 4985

Reaction equation

HRID 4985 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@H:30]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:31])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20]>>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@H:30]([C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[CH3:31])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

3

Reactant 2

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 131717745H-Gly-Leu-Ala-OBzl

Product 1

HCID 131717746Boc-Leu-Gly-Leu-Ala-OBzl

Procedure

Boc-Leu-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Leu-OH (2.62 g, 10.5 mmoles) to H-Gly-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The resulting product was crystallized from ethyl acetate:hexane to yield 2.7 g (mp 95°-96°) in the first crop.

Workup

  1. customThe resulting product was crystallized from ethyl acetate
  2. customhexane to yield 2.7 g (mp 95°-96°) in the first crop

Sources & evidence

ORD record
ord-dcb3efb5c2714b649c6024418e3d449a
Source dataset
uspto-grants-1993_09
Patent number
US05242904

Linked notes

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