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

HRID 971561Notes

Reaction equation

HRID 971561 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-7f0a82ca60bb40c8a9b28a72fbacdcd3
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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