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

HRID 1686014Notes

Reaction equation

HRID 1686014 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-93398cc0b4904afeb20a5821b435a33f
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

Loading…