Z-Asn-onp → HCID 178501420, compound

HRID 1580883Notes

Reaction equation

HRID 1580883 reaction equation
[NH2:1][C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:36]([O:38][CH3:39])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:40]1[CH:45]=[CH:44][C:43]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:56](OC2C=CC([N+]([O-])=O)=CC=2)=[O:57])[CH2:52][C:53]([NH2:55])=[O:54])=[O:49])=[CH:42][CH:41]=1>CN(C)C=O>[NH:50]([C:48]([O:47][CH2:46][C:43]1[CH:44]=[CH:45][CH:40]=[CH:41][CH:42]=1)=[O:49])[C@H:51]([C:56]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:36]([O:38][CH3:39])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[O:57])[CH2:52][C:53](=[O:54])[NH2:55]

Participants

4

Reactant 2

HCID 7021351Z-Asn-onpHCID 178501423HCID 178501423, compound

Product 1

HCID 178501420HCID 178501420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.4 g of H-Lys(BOC)-Phe-His-OMe (compare Example 1) and 4.5 g of Z-Asn-ONP in 20 ml of dimethylformamide are stirred for 20 hours at room temperature. The peptide derivative is precipitated by adding ethyl acetate, filtered off and washed with ether. After recrystallisation from methanol the product melts at 182°-183°C. In a thin layer chromatogram RF100 = 0.57 (on silica gel). [α]D20 = -28° (c = 1 in dimethylformamide).

Workup

  1. customThe peptide derivative is precipitated
  2. additionby adding ethyl acetate
  3. filtrationfiltered off
  4. washwashed with ether
  5. customAfter recrystallisation from methanol the product melts at 182°-183°C

Sources & evidence

ORD record
ord-42e68ad76cc94dbca9411a5a2b44d3b4
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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