Methanol → HCID 68430706, compound

HRID 2243799Notes

Reaction equation

HRID 2243799 reaction equation
[NH2:1][C:2]([CH2:14][F:15])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:20]O>>[NH2:1][C:2]([CH2:14][F:15])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:3]([O:5][CH3:20])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 13065226HCID 13065226, compound

Product 1

HCID 68430706HCID 68430706, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-2-(fluoromethyl)-3-(3-hydroxyphenyl)propanoic acid (1 g, 4.7 mmol) in MeOH (10 mL) was added thionyl chloride (3.9 mL, 54 mmol) dropwise and the reaction mixture was heated to 60° C. for 48 h. Additional thionyl chloride (2 mL) was added and the reaction continued for 48 h. Quenching with H2O, concentration and trituration from MeCN gave methyl 2-amino-2-(fluoromethyl)-3-(3-hydroxyphenyl)propanoate. 1H NMR (400 MHz, CDCl3) δ 7.20 (m, 2H), 6.66 (m, 2H), 4.83-4.37 (ABX, J=46 Hz, J=8.8 Hz, 2H), 3.76 (s, 3H), 3.04 (d, J=13 Hz, 1H), 2.69 (d, J=13 Hz, 1H).

Workup

  1. customQuenching with H2O, concentration and trituration from MeCN

Sources & evidence

ORD record
ord-f8de98bb428b42f2b775ee0b94ac2bf7
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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