Sodium borohydride → (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

HRID 1779170노트

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HRID 1779170 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([OH:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 90060103(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid

생성물 1

HCID 90060149(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid수율 59%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

Under a nitrogen atmosphere, methanol (2.0 mL) was added to (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid (No. 5444958; 20.0 mg, 0.0302 mmol) and the mixture was cooled to 0° C. While maintaining the temperature at 0° C., sodium borohydride (1.14 mg, 0.0302 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched by adding water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA) to obtain (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5534088; 11.9 mg, 59% yield).

후처리

  1. temperatureWhile maintaining the temperature at 0° C.
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA)

출처 및 근거

ORD 기록
ord-16b98b186d2541e386d230e620505e78
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266853B2

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