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

HRID 864674

反応式

HRID 864674 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-12ae1735501e41308e44f3783b23eef8
出典データセット
uspto-grants-1996_10
特許番号
US05563278

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