Methanol → Methyl D-2-(4-fluorophenyl)glycinate

HRID 405907Notes

Reaction equation

HRID 405907 reaction equation
[CH:1]1[C:6]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=[C:3]([F:12])[CH:2]=1.S(Cl)(Cl)=O.[CH3:17]O>>[NH2:11][C@H:7]([C:6]1[CH:5]=[CH:4][C:3]([F:12])=[CH:2][CH:1]=1)[C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 124515Amino(4-fluorophenyl)acetic acid

Product 1

HCID 11049834Methyl D-2-(4-fluorophenyl)glycinate

Procedure

4 g (R)-4-fluorophenylglycine are suspended in 80 ml of methanol. While cooling with the ice bath 3.28 ml of thionyl chloride are slowly added dropwise, so that the temperature is maintained between 15° C. and 20° C. The reaction mixture is stirred for 12 hours at ambient temperature and then evaporated to dryness. 5.1 g of the product are obtained as the hydrochloride. Analytical HPLC-MS (method A): RT=0.8 min.

Workup

  1. additionare slowly added dropwise, so that the temperature
  2. temperatureis maintained between 15° C. and 20° C
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-ddcf70ab5c3b43cdb9d11a0ae8875362
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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