Pyridine → (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate

HRID 1699972노트

반응식

HRID 1699972 반응식
[C:1]([O:4][CH2:5][C@@H:6]([OH:23])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].N1C=CC=CC=1>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@@H:6]([O:23][S:25]([CH3:24])(=[O:27])=[O:26])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 11056398(2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane

생성물 1

HCID 11475108(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate수율 98.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture composed of 12.4 mmol (4.00 g) of (2S, 3S)-1-acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane, 24.8 mmol (2.48 g) of methanesulfonyl chloride and 20 ml of pyridine was allowed to stand at 4° C. for 48 hours. Thereafter, 30 ml of ethyl acetate was added, the organic layer was washed with three 30-ml portions of 10% hydrochloric acid and finally with 30 ml of water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. Hexane (30 ml) was added to the residue, and the mixture was allowed to stand. The resulting white solid precipitate was collected by filtration. Thus was obtained 4.90 g (98%) of the title compound.

후처리

  1. washthe organic layer was washed with three 30-ml portions of 10% hydrochloric acid and finally with 30 ml of water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionHexane (30 ml) was added to the residue
  7. filtrationThe resulting white solid precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-bb87693aa70c4dc6b41e52b9cddc5c79
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348615B2

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