Water → (+/-)-tert-Butyl 1-[3-({cyclopentyl[4-(2,2-difluorovinyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylate

HRID 1475657ノート

反応式

HRID 1475657 の反応式
Cl[C:2]([F:7])([F:6])[C:3]([O-])=O.[Na+].[CH:9]1([CH:14]([C:35]2[CH:40]=[CH:39][C:38](C=O)=[CH:37][CH:36]=2)[C:15]([NH:17][C:18]2[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=2)[CH2:21][C:22]2([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]2)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(OCC)(=O)C>[CH:9]1([CH:14]([C:35]2[CH:40]=[CH:39][C:38]([CH:3]=[C:2]([F:7])[F:6])=[CH:37][CH:36]=2)[C:15]([NH:17][C:18]2[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=2)[CH2:21][C:22]2([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 2734985Sodium chlorodifluoroacetateHCID 86667523(+/-)-Tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate

生成物 1

HCID 66563353(+/-)-tert-Butyl 1-[3-({cyclopentyl[4-(2,2-difluorovinyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

At 60° C., 475.6 mg (3.12 mmol) of sodium chloro(difluoro)acetate were added to a mixture of 800.0 mg (1.73 mmol) of (+/−)-tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate and 681.9 mg (2.60 mmol) of triphenylphosphine. The mixture was heated to 110° C. and stirred at this temperature for 30 min. After cooling, the mixture was poured into water. Ethyl acetate was added, and the organic phase was separated off, washed with saturated sodium chloride solution, dried with magnesium sulphate and concentrated under reduced pressure. The crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 319.2 mg (37.2% of theory) of the target compound.

後処理

  1. temperatureAfter cooling
  2. customthe organic phase was separated off
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water)

出典と根拠

ORDレコード
ord-34afe3328bf447babdfd93a21b882cbc
出典データセット
uspto-grants-2015_04
特許番号
US09018258B2

反応ノート

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