Glyoxylic acid, monohydrate → N-{2-[(ethyloxy)carbonyl]-5-[(4-fluorophenyl)methyl]-3-pyridinyl}glycine

HRID 2364202Notes

Reaction equation

HRID 2364202 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.O.[C:22]([OH:26])(=[O:25])[CH:23]=O>>[CH2:19]([O:18][C:16]([C:3]1[C:2]([NH:1][CH2:23][C:22]([OH:26])=[O:25])=[CH:7][C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[CH:5][N:4]=1)=[O:17])[CH3:20]

Participants

3

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 42637772Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

Product 1

HCID 58882950N-{2-[(ethyloxy)carbonyl]-5-[(4-fluorophenyl)methyl]-3-pyridinyl}glycine

Procedure

This compound was prepared from ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate and glyoxylic acid monohydrate employing methods similar to those described in Example 11, Step 1 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 13.1 (1H, br), 7.91 (1H, t, J=5 Hz), 7.78 (1H, d, J=1 Hz), 7.29 (2H, dd, J=9, 6 Hz), 7.09 (1H, t, J=9 Hz), 7.02 (1H, s), 4.25 (2H, q, J=7 Hz), 3.92 (2H, d, J=5 Hz), 3.90 (2H, s), 1.27 (3H, t, J=7 Hz); ES+ MS: 333 (M+1).

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-6887897ed04f4589a179f350596959c5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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