Methanol → (S)-methyl 3-amino-2-hydroxypropanoate hydrochloride

HRID 1752411Notes

Reaction equation

HRID 1752411 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:7])[C:4]([OH:6])=[O:5].O=S(Cl)[Cl:10].[CH3:12]O>>[ClH:10].[NH2:1][CH2:2][C@H:3]([OH:7])[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 6999797L-Isoserine

Product 1

HCID 71757488(S)-methyl 3-amino-2-hydroxypropanoate hydrochloride

Procedure

To an ice-cooled suspension of (S)-3-amino-2-hydroxypropanoic acid (0.904 g) in MeOH (15 mL) was added SOCl2 (2.0 mL, 27 mmol) over ˜2.5 minutes. After the addition the reaction was allowed to warm to room temperature. After stirring overnight, the reaction was evaporated in vacuo. MeOH was added and the mixture evaporated in vacuo a second time to yield the product (S)-methyl 3-amino-2-hydroxypropanoate hydrochloride as a colorless oil. 1H NMR (400 MHz, DMSO-d6): 8.16 (3H, s), 6.36 (1H, s), 4.38 (1H, br d, J=8.3 Hz), 3.68 (3H, s), 3.10 (1H, dd, J=12.9 Hz, 3.7 Hz), 2.90 (1H, dd, J=12.9 Hz, 8.6 Hz).

Workup

  1. additionAfter the addition the reaction
  2. customthe reaction was evaporated in vacuo
  3. additionMeOH was added
  4. customthe mixture evaporated in vacuo a second time

Sources & evidence

ORD record
ord-629d84f1222e4dd8b7bd0807c2019986
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

Loading…