HCID 18929217, compound → N-o-Fluorophenylglycine

HRID 1599824Notes

Reaction equation

HRID 1599824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([O:12]CC1C=CC=CC=1)=[O:11]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 18929217HCID 18929217, compound

Product 1

HCID 5171030N-o-FluorophenylglycineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 10% Pd/C (200 mg) in reagent grade methanol (25 mL) which was degassed was added a solution of benzyl 2-((2-fluorophenyl)amino)acetate from Example 48 (2.0 g, 7.71 mmol) in methanol (10+5 mL). The solution was degassed, a balloon of hydrogen gas was added, and then the reaction mixture was stirred for 8 h at rt. The reaction mixture was filtered though celite and then concentrated to yield 1.27 g (97%) of the title compound as a white solid: mp 125.7°-126.6° C. (lit. 122°-123° C. (Walls, L. P. South African patent application 664864; Walls, L. P. GB 1,153,884); 1H NMR (CDCl3) δ7.06-6.99 (m, 2H), 6.77-6.70 (m, 1H), 6.33 (dt, J=8.8, J=1.2, 1H), 4.04 (s, 2H); 13C NMR (CDCl3) δ175.79, 151.71 (d, J=239); 135.01, 124.65 (d, J=3.5), 118.38 (d, J=6.4), 114.85 (d, J=18.4), 112.45, 45.30; MS (EI, m/z) 169 (M+). HRMS (EI) calcd for C8H8NO2F 169.0539, found 169.0538.

Workup

  1. customwas degassed
  2. customThe solution was degassed
  3. additiona balloon of hydrogen gas was added
  4. filtrationThe reaction mixture was filtered though celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c4eac12e6bf04b30b3264dd3bf8b5b34
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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