O-Benzylhydroxylamine → HCID 86756905, compound

HRID 1979214Notes

Reaction equation

HRID 1979214 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([N:16]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:17][C:18](=[O:37])[C@@H:19]([CH:24]([C:34](O)=[O:35])[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:42]([O:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([N:16]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:17][C:18](=[O:37])[C@@H:19]([CH:24]([C:34](=[O:35])[NH:50][O:49][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:20][CH:21]([CH3:22])[CH3:23])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 102313O-BenzylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69951124HCID 69951124, compound

Product 1

HCID 86756905HCID 86756905, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.15 g of 2′-(N-benzyloxycarbonyl-D-alanyl)-2(R)-[1(RS)-(carboxy)-4-phenylbutyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of dimethylformamide was cooled to 0° C. under a nitrogen atmosphere. The mixture was then treated with 1.25 g of O-benzylhydroxylamine and 0.467 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and left to warm to room temperature overnight. The mixture was diluted with water and extracted twice with ethyl acetate. The ethyl acetate layer was then washed with aqueous 2M hydrogen chloride, water and brine. Drying over anhydrous magnesium sulphate and evaporation of the solvent gave 0.820 g of 2′-(N-benzyloxycarbonyl-D-alanyl)-2(R)-[1(RS)-[(benzyloxy)carbamoyl)-4-phenylbutyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. waitleft
  2. extractionextracted twice with ethyl acetate
  3. washThe ethyl acetate layer was then washed with aqueous 2M hydrogen chloride, water and brine
  4. dry with materialDrying over anhydrous magnesium sulphate and evaporation of the solvent

Sources & evidence

ORD record
ord-b8e0c788b0624afb902b68708fd92646
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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