Water → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1,4-oxazepane-4-carboxylate

HRID 1022708ノート

反応式

HRID 1022708 の反応式
[NH2:1][C:2](=[N:26][OH:27])[CH2:3][C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1.[CH3:28][C:29](C)([O-])C.[K+].C(OCC)(=O)C.O>C1(C)C=CC=CC=1>[Cl:18][C:13]1[CH:12]=[C:11]([C@@H:10]2[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:5][C@H:4]2[CH2:3][C:2]2[N:1]=[C:28]([CH3:29])[O:27][N:26]=2)[CH:16]=[CH:15][C:14]=1[Cl:17]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 86663870tert-butyl (6R,7R)-6-[2-amino-2-(hydroxyimino)ethyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

生成物 1

HCID 66975054tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1,4-oxazepane-4-carboxylate収率 44.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of tert-butyl (6R,7R)-6-[2-amino-2-(hydroxyimino)ethyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (388 mg, 0.93 mmol) in toluene (4 mL) were added potassium tert-butoxide (208 mg, 1.86 mmol) and ethyl acetate (1 mL, 0.93 mmol). The reaction mixture was stirred at 100° C. overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (183.4 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8a01925d028f401f8bd52d60c27b241f
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

反応ノート

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