Sodium hydride → HCID 131735581, 화합물

HRID 524362노트

반응식

HRID 524362 반응식
[H-].[Na+].[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[NH:23]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1>CN(C=O)C>[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[N:23]1[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 67300712HCID 67300712, 화합물HCID 131735580(R)-3-(((tert-Butyldiphenylsilyl)oxy)methyl)isothiazolidine 1,1-dioxide

생성물 1

HCID 131735581HCID 131735581, 화합물수율 92.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

To a mixture of sodium hydride (37 mg, 1.54 mmol) in DMF (3.0 mL) cooled to 0° C. was added dioxide 8 (554 mg, 1.42 mmol). After 0.5 h a solution methyl 5-(3-iodopropyl)thiophene-2-carboxylate (485 mg, 1.56 mmol) in DMF (4.5 mL). The reaction was allowed to warm to room temperature on its own accord and stirred for 16 h. The reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex) afforded 751 mg (91%) of ester 9.

후처리

  1. temperatureto warm to room temperature on its own accord
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with EtOAc
  4. washThe organic portion was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex)

출처 및 근거

ORD 기록
ord-5615229e6e034aa0ba265a1ceaead14b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340534B2

반응 노트

불러오는 중…