Ethyl Acetate → HCID 178523867, compound

HRID 64830Notes

Reaction equation

HRID 64830 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.[OH:52][CH2:53][CH2:54][NH:55][C:56]([C@@H:58]1[CH2:62][CH2:61][CH2:60]N1)=[O:57]>CN(C=O)C>[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:25]([N:27]1[CH2:60][CH2:61][CH2:62][C@H:58]1[C:56]([NH:55][CH2:54][CH2:53][OH:52])=[O:57])=[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 12136434(S)-N-(2-Hydroxyethyl)pyrrolidine-2-carboxamideHCID 178514453HCID 178514453, compoundHCID 178514642N-cbz-l-histidyl azide

Product 1

HCID 178523867HCID 178523867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ethyl acetate solution of Nα -benzyloxycarbonyl-L-histidinazide (4) prepared from Nα -benzyloxycarbonyl-L-histidine hydrazide (3) (6.07 g) by a known method was added 10 ml of a DMF solution of 2.31 g of (S)-N-(2-hydroxyethyl)-2-pyrrolidinecarboxamide (53) under ice-cooling and they were reacted 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), 3.43 g of Nα -benzyloxycarbonyl-L-histidyl-N-(2-hydroxyethyl)-L-prolinamide (54) was obtained.

Workup

  1. temperaturecooling
  2. customthey were reacted 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-fd0484b57bd14994b07788ba22b8ef20
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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