Hydrochloric Acid → Propanoic acid, 3-amino-2,2-difluoro-, methyl ester, hydrochloride (1:1)

HRID 1880987Notes

Reaction equation

HRID 1880987 reaction equation
[NH2:1][CH2:2][C:3]([F:8])([F:7])[C:4]([OH:6])=[O:5].O=S(Cl)[Cl:11].Cl.[CH3:14]O>>[ClH:11].[NH2:1][CH2:2][C:3]([F:8])([F:7])[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24386Thionyl ChlorideHCID 27564053-Amino-2,2-difluoropropanoic acid

Product 1

HCID 22635305Propanoic acid, 3-amino-2,2-difluoro-, methyl ester, hydrochloride (1:1)

Procedure

In a round bottom flask, 3-amino-2,2-difluoropropanoic acid (500 mg, 4 mmol) was solubilized in MeOH (10 mL). At 0° C., SOCl2 (1 mL) was added dropwise. The reaction mixture was then stirred at room temperature overnight. Evaporation of the reaction mixture gave a white solid to be the product as HCl salt (570 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.63 (t, J=16 Hz, 2 H) 3.87 (s, 3 H) 9.07 (br. s., 2 H).

Workup

  1. customEvaporation of the reaction mixture
  2. customgave a white solid

Sources & evidence

ORD record
ord-2757326088424fa6a5abad79385ea8e3
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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