Hydrochloric Acid → 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid

HRID 1651017ノート

反応式

HRID 1651017 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:27][CH3:28])[C:22]([O:24]CC)=[O:23])[O:13][C:12]1([CH3:30])[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C(O)C.O.[OH-].[K+]>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:27][CH3:28])[C:22]([OH:24])=[O:23])[O:13][C:12]1([CH3:30])[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 70040836ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoate

生成物 1

HCID 571587953-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid

試薬・触媒・溶媒 2

HCID 14797Potassium Hydroxide溶媒HCID 19096565Water ethanol溶媒

実験手順

517 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoate was dissolved in 3.10 ml of an ethanol/water (9/1) solution of 2N potassium hydroxide, and the mixture was stirred for 3 hours at room temperature. The reaction solution was adjusted to pH 2 with 1N hydrochloric acid under cooling with ice. Then, 24 ml of water was added thereto and extracted three times with 20 ml of ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2propenoic acid as a colorless oily substance.

後処理

  1. temperatureunder cooling with ice
  2. extractionextracted three times with 20 ml of ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-910163755a344ba6b81f914995f78ea5
出典データセット
uspto-grants-1990_05
特許番号
US04927565

反応ノート

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