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Acetic Acid → ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888297
ノート
印刷プレビュー

反応式

HRID 1888297 の反応式
[CH3:1][C:2]([CH3:30])([CH2:26][CH2:27][CH2:28][CH3:29])[C:3](=[O:25])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.[BH4-].[Na+].C(O)(=O)C.O>CO>[OH:25][C@@H:3]([C:2]([CH3:1])([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66857555ethyl 2-[(2-{(4S)-4-[(1E)-4,4-dimethyl-3-oxo-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

生成物 1

HCID 66857441ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of the compound 6 (124 mg) in anhydrous methanol (1.40 mL) were added sodium borohydride (10.4 mg) and a catalytic amount of acetic acid at −78° C. and the solution was stirred at the same temperature for 1 hour. After return to room temperature, to the reaction solution was added water and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1), to give the title compound (87.2 mg) having the following physical data.

後処理

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-a8e32cd44aac4bd8aaef27881b234cc8
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08501793B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート