Ethyl Acetate → HCID 178523866, compound

HRID 64842Notes

Reaction equation

HRID 64842 reaction equation
C(OCC)(=O)C.[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:25]([N:27]=[N+]=[N-])=[O:26])[CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OC(N[C@H](C(NN)=O)CC1N=CNC=1)=O)C1C=CC=CC=1.[O:52]=[C:53]1[CH2:57][CH2:56][CH2:55][N:54]1[CH2:58][CH2:59][CH2:60][NH:61][C:62]([C@@H:64]1[CH2:68][CH2:67][CH2:66]N1)=[O:63]>CN(C=O)C>[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:25]([N:27]1[CH2:66][CH2:67][CH2:68][C@H:64]1[C:62]([NH:61][CH2:60][CH2:59][CH2:58][N:54]1[CH2:55][CH2:56][CH2:57][C:53]1=[O:52])=[O:63])=[O:26])[CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 53958674(S)-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-2-pyrrolidinecarboxamideHCID 178514453HCID 178514453, compoundHCID 178514642N-cbz-l-histidyl azide

Product 1

HCID 178523866HCID 178523866, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 30 ml of a ethyl acetate solution of compound (4) prepared from 2.12 g of compound (3) by a known method was added 5 ml of a DMF solution of 1.17 g of compound (100) 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-aqueous ammonia (90:10:1), 2.00 g of Nα -benzyloxycarbonyl-L-histidyl-N-[3-(2-oxo-1-pyrrolidinyl)-propyl]-L-prolinamide (101) 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-aqueous ammonia (90:10:1)

Sources & evidence

ORD record
ord-66e7a2796bc14565aa220b4acc06dbde
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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