Benzilic acid → alpha-Hexyl-4-[(diphenylhydroxyacetyl)amino]-1H-imidazole-1-acetic acid ethyl ester

HRID 864674

Reaction equation

HRID 864674 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]([OH:17])([C:14]([OH:16])=O)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([O:32][C:33](=[O:47])[CH:34]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[N:35]1[CH:39]=[C:38]([NH2:40])[N:37]=[CH:36]1)[CH3:31]>CN(C=O)C>[CH2:30]([O:32][C:33](=[O:47])[CH:34]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[N:35]1[CH:39]=[C:38]([NH:40][C:14](=[O:16])[C:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[OH:17])[N:37]=[CH:36]1)[CH3:31]

Participants

5

Reactant 3

HCID 6463Benzilic acidHCID 682631,1'-CarbonyldiimidazoleHCID 15222343ethyl 2-(4-amino-1H-imidazol-1-yl)octanoate

Product 1

HCID 53913468alpha-Hexyl-4-[(diphenylhydroxyacetyl)amino]-1H-imidazole-1-acetic acid ethyl esterYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4.6 g of benzylic acid, 3.2 g of 1,1'-carbonyldiimidazole, and 150 ml of DMF were mixed and stirred for 1 hour. A solution of 5.0 g of 4-amino-α-hexyl-1H-imidazole-1-acetic acid ethyl ester in DMF was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, ethyl acetate was added, and the organic solution was washed sequentially with water, a 10% sodium hydroxide solution, and water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by HPLC eluting with 30% ethyl acetate in toluene. The appropriate fractions were combined and concentrated in vacuo to provide 1.4 g of the desired titled product.

Workup

  1. additionwere mixed
  2. stirringthe mixture stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated in vacuo, ethyl acetate
  4. additionwas added
  5. washthe organic solution was washed sequentially with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC
  9. washeluting with 30% ethyl acetate in toluene
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12ae1735501e41308e44f3783b23eef8
Source dataset
uspto-grants-1996_10
Patent number
US05563278

Linked notes

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