O-Benzylhydroxylamine → HCID 86757338, compound

HRID 651830Notes

Reaction equation

HRID 651830 reaction equation
[C:1]([C@H:4]([C@@H:14]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:15]([NH:17][N:18]1[C:22](=[O:23])[CH2:21][N:20]([CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:19]1=[O:29])=[O:16])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(O)=[O:2].[CH2:34]([O:41][NH2:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O.C(OCC)(=O)C.Cl.C(N=C=NCCCN(C)C)C>[CH2:34]([O:41][NH:42][C:1]([C@H:4]([C@@H:14]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:15]([NH:17][N:18]1[C:22](=[O:23])[CH2:21][N:20]([CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[C:19]1=[O:29])=[O:16])[CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:2])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 70202725HCID 70202725, compound

Product 1

HCID 86757338HCID 86757338, compoundYield 32.9%

Reagents, catalysts & solvents 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.151 g of 2(R)-[1(S)-(carboxy)-4-phenylbutyl]-N-[3-[2-(dimethylamino)ethyl]-2,5-dioxo-1-imidazolidinyl]-4-methylvaleramide and 0.157 g of O-benzylhydroxylamine in 0.25 ml of dimethylformamide was treated with 0.054 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride and stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and evaporated to give a residue which was purified by flash column chromatography on silica gel, using methanol/dichloromethane (5:95) for the elution, to give 0.061 g of 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-N-[3-[2-(dimethylamino)ethyl]-2,5-dioxo-1-imidazolidinyl]-4-methylvaleramide in the form of a white foam.

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customto give a residue which
  5. customwas purified by flash column chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-ed17db1815ed4acf917c58e7c213dd41
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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