Ethyl bromoacetate → {5-[Ethoxycarbonylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

HRID 15531

反応式

HRID 15531 の反応式
[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:38]([O:40][C:41](=[O:44])[CH2:42]Br)[CH3:39]>CN(C=O)C>[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:42][C:41]([O:40][CH2:38][CH3:39])=[O:44])[S:18]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)(=[O:19])=[O:20])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetate2 回HCID 11430Potassium Carbonate2 回HCID 67201670[5-(4-Fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

生成物 1

HCID 67201391{5-[Ethoxycarbonylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The product from example 1, step d.) (50 mg, 0.111 mmol) was dissolved in DMF (1 mL), treated with K2CO3 (23 mg, 0.167 mmol), bromo-acetic acid ethyl ester (25 uL, 0.133 mmol), and stirred at ambient temperature overnight. The reaction was heated to 50° C. for 2 hours, then more K2CO3 (23 mg, 0.167 mmol) and bromo-acetic acid ethyl ester (25 uL, 0.133 mmol) were added and the reaction was heated to 80° C. for three hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed several times with water and concentrated under reduced pressure to give the sub-title compound that was used in crude form without purification.

後処理

  1. temperatureThe reaction was heated to 50° C. for 2 hours
  2. temperaturethe reaction was heated to 80° C. for three hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed several times with water
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-692e03e384d5438e812d91b10a28160e
出典データセット
uspto-grants-2010_06
特許番号
US07732618B2

関連ノート

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