Ethanol → (S)-2-amino-4-bromo-butyric acid ethyl ester hydrochloride

HRID 1686013Notes

Reaction equation

HRID 1686013 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)[CH3:15]>>[ClH:12].[CH2:14]([O:5][C:4](=[O:6])[C@@H:3]([NH2:2])[CH2:7][CH2:8][Br:9])[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2733672(S)-(+)-2-Amino-4-bromobutyric Acid Hydrobromide

Product 1

HCID 86630464(S)-2-amino-4-bromo-butyric acid ethyl 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 ethanol (10 ml), at 0° C., was added thionyl chloride (1.11 ml, 15.21 mmol). The solution was stirred at 70° C. for 1 hour, cooled and concentrated in vacuo. Heptane added and mixture concentrated under high vac. Ether was added and the precipitate stirred for 1 hr, filter and dried in vacuo to provide (S)-2-amino-4-bromo-butyric acid ethyl ester hydrochloride as an sticky white solid (1.9 g).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionHeptane added
  4. concentrationmixture concentrated under high vac
  5. additionEther was added
  6. stirringthe precipitate stirred for 1 hr
  7. filtrationfilter
  8. customdried in vacuo

Sources & evidence

ORD record
ord-13be7a2fdd5e43d2a9a4f5f0c952cdea
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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