L-Prolinanilide → HCID 178523864, compound

HRID 64838Notes

Reaction equation

HRID 64838 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([N:21]=[N+]=[N-])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N[C@H](C(NN)=O)CC1N=CNC=1)=O)C1C=CC=CC=1.[C:46]1([NH:52][C:53]([C@@H:55]2[CH2:59][CH2:58][CH2:57]N2)=[O:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([N:21]1[CH2:57][CH2:58][CH2:59][C@H:55]1[C:53]([NH:52][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:54])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6552381L-ProlinanilideHCID 178514453HCID 178514453, compoundHCID 178514642N-cbz-l-histidyl azide

Product 1

HCID 178523864HCID 178523864, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 45 ml of an ethyl acetate solution of Nα -benzyloxycarbonyl-L-histidine azide (4) prepared from 3.03 g of Nα -benzyloxycarbonyl-L-histidine hydrazide (3) by a known method was added 1.52 g of compound (94) under ice-cooling and the reaction was maintained overnight in a refrigerator. The reaction mixture was concentrated and the residue thus formed was subjected to silica gel column chromatography. By eluting the product with chloroform-methanol (95:5), 2.49 g of Nα -benzyloxycarbonyl-L-histidyl-N-phenyl-L-prolinamide (95) was obtained.

Workup

  1. temperaturecooling
  2. temperaturethe reaction was maintained overnight in a refrigerator
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue thus formed
  5. washBy eluting the product with chloroform-methanol (95:5)

Sources & evidence

ORD record
ord-ca41debf21784614b7caddf17a89fd4d
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

Loading…