Hydrogen Bromide → (S)-(+)-2-Amino-4-bromobutyric Acid Hydrobromide

HRID 1171955Notes

Reaction equation

HRID 1171955 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8].[BrH:9]>CC(O)=O>[BrH:9].[NH2:2][C@@H:3]([CH2:7][CH2:6][Br:9])[C:4]([OH:5])=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 2733667L-Homoserine lactone hydrochloride

Product 1

HCID 2733672(S)-(+)-2-Amino-4-bromobutyric Acid HydrobromideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-3-aminodihydrofuran-2(3H)-one hydrochloride (10.30 g, 74.87 mmol) in 58 mL of 30% w/w HBr in HOAc was stirred at 65° C. for 30 hrs. The solvent was removed under reduced pressure and the resulted solid was suspended in MTBE (200 mL) and stirred for 30 min. The solid was collected by filtration and washed with MTBE (200 mL) and dried to give (S)-2-amino-4-bromobutanoic acid hydrobromide as white solid (19.33 g, 98%). 1H NMR (400 MHz, d6-DMSO) δ8.37 (s, 3H), 4.01 (m, 1H), 3.65 (m, 2H), 2.33 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe solid was collected by filtration
  3. washwashed with MTBE (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-1a37dae5de404242af16ed2417d68b3e
Source dataset
uspto-grants-2010_11
Patent number
US07829665B2

Reaction notes

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