Tetrabutylammonium Fluoride → (4S,5S)-tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-4-((5-propylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

HRID 1009118

反応式

HRID 1009118 の反応式
[Si]([C:8]1[S:9][C:10]([CH2:37][CH2:38][CH3:39])=[C:11]([CH2:13][C@H:14]2[C@@H:18]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[O:17][C:16]([CH3:29])([CH3:28])[N:15]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:20][CH2:19][C@H:18]1[O:17][C:16]([CH3:29])([CH3:28])[N:15]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[C@H:14]1[CH2:13][C:11]1[N:12]=[CH:8][S:9][C:10]=1[CH2:37][CH2:38][CH3:39]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67304570(4S,5S)-tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

生成物 1

HCID 59347039(4S,5S)-tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-4-((5-propylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate was dissolved in THF (3 mL) and cooled to 0° C. when TBAF (0.808 ml, 0.808 mmol) was added. The reaction was stirred one hour before being quenched with saturated ammonium chloride. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine and dried over sodium sulfate to afford the title compound.

後処理

  1. additionwas added
  2. custombefore being quenched with saturated ammonium chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-5629902611ee45aabf5b9f5e0c27346a
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

関連ノート

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