Trifluoroacetic acid → Benzyl (3R)-6-(2,3-difluorophenyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

HRID 493641

反応式

HRID 493641 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C:16]1[CH2:22][N:21](CC2C=CC(OC)=CC=2OC)[C:20](=[O:34])[C@H:19]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:18][CH:17]=1>ClCCl>[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C:16]1[CH2:22][NH:21][C:20](=[O:34])[C@H:19]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:18][CH:17]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86595036Benzyl (3R)-6-(2,3-difluorophenyl)-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

生成物 1

HCID 86595037Benzyl (3R)-6-(2,3-difluorophenyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate収率 66.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (60 mL) was added to a solution of benzyl (3R)-6-(2,3-difluorophenyl)-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (3.70 g, 7.08 mmol) in dichloromethane (40 mL). After 18 h, the mixture was concentrated at 25° C., methanol (150 mL) was added, and the precipitate filtered. The filtrate was concentrated, diluted with dichloromethane (100 mL), washed with water (2×), saturated aqueous sodium bicarbonate (2×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes→65% ethyl acetate/hexanes) gave the title compound (1.75 g). MS 373.1 (M+1).

後処理

  1. concentrationthe mixture was concentrated at 25° C.
  2. additionmethanol (150 mL) was added
  3. filtrationthe precipitate filtered
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with dichloromethane (100 mL)
  6. washwashed with water (2×), saturated aqueous sodium bicarbonate (2×), saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (5% ethyl acetate/hexanes→65% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-613ca6ebf52545a2848f93214a37c30e
出典データセット
uspto-grants-2009_05
特許番号
US07534784B2

関連ノート

読み込み中…