Hydrochloric Acid → Methyl D-2-(4-fluorophenyl)glycinate

HRID 1373737Notes

Reaction equation

HRID 1373737 reaction equation
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Cl.[CH3:14]O>>[CH3:14][O:4][C:3](=[O:5])[C@H:2]([NH2:1])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 124515Amino(4-fluorophenyl)acetic acid

Product 1

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

Procedure

(R)-Amino-(4-fluoro-phenyl)-acetic acid was treated with HCl gas (8 g) dissolved in methanol at room temperature for 24 hours. The reaction mixture was concentrated and aqueous sodium bicarbonate was added until the pH of the mixture remained basic. The aqueous layer was extracted three times with dichloromethane. The combined extracts were dried (Na2SO4) and concentrated afford the title compound as an oil. 1HNMR (400 MHz, CDCl3)δ 1.90 (br s, 2H), 3.67 (s, 3H), 4.58 (s, 1H), 7.00 (m, 2H), 7.30 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionaqueous sodium bicarbonate was added until the pH of the mixture
  3. extractionThe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40d41a23026a4ddea84368ec91b3e7bf
Source dataset
uspto-grants-2007_01
Patent number
US07163942B2

Reaction notes

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