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

HRID 1009118

반응식

HRID 1009118 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-5629902611ee45aabf5b9f5e0c27346a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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