L-Alanine → 2-Methylpropyl (2S)-2-aminopropanoate hydrochloride

HRID 515950Notes

Reaction equation

HRID 515950 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O=S(Cl)[Cl:9].[CH2:11](O)[CH:12]([CH3:14])[CH3:13]>>[ClH:9].[NH2:1][C@@H:2]([CH3:3])[C:4]([O:6][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:5]

Participants

4

Reactant 3

HCID 5950L-AlanineHCID 6560IsobutanolHCID 24386Thionyl Chloride

Product 1

HCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochlorideYield 97%

Conditions

Temperature
85 °C

Procedure

To a solution of L-alanine (11.22 mmol) in isobutanol (30 mL) at 0° C. was added SOCl2 (56.12 mmol) dropwise. The reaction mixture was stirred at 85° C. during 17 hours. The reaction was cooled down to room temperature and concentrated under reduced pressure. Co-evaporations with toluene were done and the yellow solid was washed with petroleum ether and dried under vacuum to give the expected salt in 97% yield. 1H NMR (DMSO, 400 MHz) δ (ppm) 0.89 (d, J=6.8 Hz, 6H), 1.42 (d, J=7.15 Hz, 3H), 1.91 (septuplet, J=6.71 Hz, 1H), 3.88-4 (m, 2H), 4.07 (q, J=7.16 Hz, 1H), 8.53 (brs, 3H).

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washthe yellow solid was washed with petroleum ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-db5b2553371e474cb6e0e1eaf9b40e1b
Source dataset
uspto-grants-2015_08
Patent number
US09109001B2

Reaction notes

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