(S)-N-Butylpyrrolidine-2-carboxamide → HCID 178449505, compound

HRID 980375Notes

Reaction equation

HRID 980375 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.[CH2:46]([NH:50][C:51]([C@@H:53]1[CH2:57][CH2:56][CH2:55]N1)=[O:52])[CH2:47][CH2:48][CH3:49]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([N:21]1[CH2:55][CH2:56][CH2:57][C@H:53]1[C:51]([NH:50][CH2:46][CH2:47][CH2:48][CH3:49])=[O:52])=[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 22691332(S)-N-Butylpyrrolidine-2-carboxamideHCID 178514453HCID 178514453, compoundHCID 178514642N-cbz-l-histidyl azide

Product 1

HCID 178449505HCID 178449505, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 75 ml of an ethyl acetate solution of Nα -benzyloxycarbonyl-L-histidine azide (4) prepared from 4.85 g of Nα -benzyloxycarbonyl-L-histidine hydrazide (3) by the method of Reference example 2 was added 2.23 g of compound (31) under ice-cooling and the mixture was placed overnight in a refrigerator to maintain the reaction. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography. By eluting the product with chloroform-methanol-aqueous ammonia (95:5:0.5), 4.13 g of Nα -benzyloxycarbonyl-L-histidyl-N-butyl-L-prolinamide was obtained.

Workup

  1. temperaturecooling
  2. temperatureto maintain
  3. customthe reaction
  4. concentrationThe reaction mixture was concentrated
  5. washBy eluting the product with chloroform-methanol-aqueous ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-1c5117dca0a847258acc19d4874b2225
Source dataset
uspto-grants-1987_01
Patent number
US04636567

Reaction notes

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