Ammonium Chloride → ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate

HRID 1173618노트

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HRID 1173618 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67105603ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-oxohexanoate

생성물 1

HCID 67105208ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate수율 89%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
-78 °C

실험 절차

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-oxohexanoate (70.68 g) in methanol (500 mL) was added sodium borohydride (9.66 g) at −78° C., and the mixture was stirred at −78° C. for 1 hr and at room temperature for 1 hr. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate (yield: 63.2 g, 89%) as a colorless solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-b019ec1f5a9b47ebbf86724b6651cdaf
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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