Z-Asn-onp → Z-Asn-Phe-NHNH-BOC

HRID 1076414Notes

Reaction equation

HRID 1076414 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][C:29]([NH:31][C@H:32]([C:37](OC2C=CC([N+]([O-])=O)=CC=2)=[O:38])[CH2:33][C:34]([NH2:36])=[O:35])=[O:30])=[CH:23][CH:22]=1>CN(C)C=O>[NH:31]([C:29]([O:28][CH2:27][C:24]1[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1)=[O:30])[C@H:32]([C:37]([NH:1][C@H:2]([C:10]([NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:38])[CH2:33][C:34](=[O:35])[NH2:36]

Participants

4

Reactant 2

HCID 7021351Z-Asn-onpHCID 131710204H-Phe-NHNH-BOC

Product 1

HCID 131710203Z-Asn-Phe-NHNH-BOC

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.4 g of H-Phe-NHNH-BOC, 1.94 g of Z-Asn-ONP and 3 ml of dimethylformamide are stirred at room temperature until the mixture solidifies. After allowing to stand overnight, the material is triturated with ether, and the dipeptide derivative is filtered off and washed with ether until free of nitrophenol. The product begins to melt at 211°C with decomposition. Rf = 0.55 in chloroform-methanol (8:2) on silica gel.

Workup

  1. customthe material is triturated with ether
  2. filtrationthe dipeptide derivative is filtered off
  3. washwashed with ether until free of nitrophenol
  4. customto melt at 211°C with decomposition

Sources & evidence

ORD record
ord-c3dfecaaed754326aa086c6b12ea780a
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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