Z-Gln-ONp → Z-Gln-Thr(tBu)-Ala-Ile-Gly-OMe

HRID 1580887Notes

Reaction equation

HRID 1580887 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:23]([NH:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[O:24])[C@H:19]([CH2:21][CH3:22])[CH3:20])=[O:16])[CH3:14])=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:38][C:39]([NH:41][C@H:42]([C:48](OC2C=CC([N+]([O-])=O)=CC=2)=[O:49])[CH2:43][CH2:44][C:45]([NH2:47])=[O:46])=[O:40])=[CH:33][CH:32]=1>CN(C)C=O.CCOCC>[NH:41]([C:39]([O:38][CH2:37][C:34]1[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=1)=[O:40])[C@H:42]([C:48]([NH:1][C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:23]([NH:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[O:24])[C@H:19]([CH2:21][CH3:22])[CH3:20])=[O:16])[CH3:14])=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:6])([CH3:8])[CH3:7])=[O:49])[CH2:43][CH2:44][C:45](=[O:46])[NH2:47]

Participants

5

Reactant 2

HCID 111333Z-Gln-ONpHCID 131709987H-Thr(tBu)-Ala-Ile-Gly-OMe

Product 1

HCID 131709986Z-Gln-Thr(tBu)-Ala-Ile-Gly-OMe

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4.6 g of the H-Thr(tBu)-Ala-Ile-Gly-OMe described under 28), in 30 ml of dimethylformamide, are mixed with 3.5 g of Z-Gln-ONP and stirred at room temperature until the mixture becomes solid. After allowing to stand overnight the mixture is diluted with ether and the precipitate is filtered off and washed with ether until free of nitrophenol. The protected pentapeptide shows Rf =0.14 in the system chloroform-methanol (95.5 ) in a thin layer chromatogram on silica gel. Melting point: >250°C.

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with ether until free of nitrophenol

Sources & evidence

ORD record
ord-622e71bbc2a04b359b3fe49e45084da6
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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