Benzyl Alcohol → (S)-2-amino-4-bromo-butyric acid benzyl ester hydrochloride

HRID 1686014노트

반응식

HRID 1686014 반응식
Br.[NH2:2][C@@H:3]([CH2:7][CH2:8][Br:9])[C:4]([OH:6])=[O:5].S(Cl)([Cl:12])=O.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[ClH:12].[CH2:14]([O:5][C:4](=[O:6])[C@@H:3]([NH2:2])[CH2:7][CH2:8][Br:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 2733672(S)-(+)-2-Amino-4-bromobutyric Acid Hydrobromide

생성물 1

HCID 67264848(S)-2-amino-4-bromo-butyric acid benzyl ester hydrochloride

반응 조건

온도
70 °C

실험 절차

To a solution of (S)-2-amino-4-bromo-butyric acid hydrobromide (2 g, 7.6 mmol) in benzyl alcohol (10 ml), at 0° C., was added thionyl chloride (1.11 ml, 15.21 mmol). The solution was stirred at 70° C. for 2 hour, cooled and concentrated in vacuo. Heptane was added and the mixture was concentrated. The oil was dissolved in toluene, ether added and initial precipitate filtered. The filtrate was allowed to stand overnight and the second precipitate filtered and dried in vacuo to provide (S)-2-amino-4-bromo-butyric acid benzyl ester hydrochloride as an off white solid (630 mg).

후처리

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionHeptane was added
  4. concentrationthe mixture was concentrated
  5. dissolutionThe oil was dissolved in toluene
  6. additionether added
  7. filtrationinitial precipitate filtered
  8. waitto stand overnight
  9. filtrationthe second precipitate filtered
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-93398cc0b4904afeb20a5821b435a33f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148531B2

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