Water → (S)-4-hydroxybutan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

HRID 245718노트

반응식

HRID 245718 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)[CH:24]=[CH:23][C:22]=1[NH:36][C:37](=[O:51])[O:38][C@H:39]([CH2:41][CH2:42][O:43][Si](C(C)(C)C)(C)C)[CH3:40].O>O1CCCC1>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([B:27]2[O:31][C:30]([CH3:32])([CH3:33])[C:29]([CH3:34])([CH3:35])[O:28]2)[CH:24]=[CH:23][C:22]=1[NH:36][C:37](=[O:51])[O:38][C@H:39]([CH2:41][CH2:42][OH:43])[CH3:40]

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67365296(S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

생성물 1

HCID 67364671(S)-4-hydroxybutan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate수율 146.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To (S)-4-(tert-butyldimethylsilyloxy)butan-2-ol (1.649 mmol, 337 mg) in dichloromethane (4 ml) were added mol sieves (4A), 2-(4-isocyanato-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.374 mmol, 378 mg) and 4-dimethylaminopyridine (0.275 mmol, 33.6 mg) were added and the mixture was stirred at 40° C. (oil bath temperature) for 18 hours. The mol sieves were removed by filtration and the filtrate washed with water, dried (sodium sulfate) and concentrated in vacuo to give a crude product which was purified by column chromatography (silica gel, heptanes with gradient 10% to 50% of ethyl acetate) to afford (S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (443 mg). Tetrabutylammonium fluoride (1M in tetrahydrofuran, 1.22 mmol, 1.22 ml) was added to (S)-4-(tert-butyldimethylsilyloxy)butan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (240 mg) in tetrahydrofuran (1 ml) at room temperature. After 20 hours water was added to the reaction mixture, extracted with dichloromethane, the organic extract dried (sodium sulfate) and concentration in vacuo to yield (S)-4-hydroxybutan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (268 mg) which was used in the next step without further purification.

후처리

  1. extractionextracted with dichloromethane
  2. extractionthe organic extract
  3. customdried
  4. concentration(sodium sulfate) and concentration in vacuo

출처 및 근거

ORD 기록
ord-523d38c473ea4fb2bad4a76c3d220b22
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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