Glyoxylic acid, monohydrate → 2-(5-Carbamoyl-2-fluorophenylamino)-2-(3-ethyl-4-fluorophenyl)acetic acid

HRID 1515567Notes

Reaction equation

HRID 1515567 reaction equation
C(C1C=C(N[CH:11](C2C=CC(OC)=C(OC)C=2)[C:12]([OH:14])=[O:13])C=CC=1)(=O)N.[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[F:35])[C:29]([NH2:31])=[O:30].[CH2:36]([C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][C:43]=1[F:44])[CH3:37].O.C(O)(=O)C=O>>[C:29]([C:28]1[CH:32]=[CH:33][C:34]([F:35])=[C:26]([NH:25][CH:11]([C:40]2[CH:41]=[CH:42][C:43]([F:44])=[C:38]([CH2:36][CH3:37])[CH:39]=2)[C:12]([OH:14])=[O:13])[CH:27]=1)(=[O:30])[NH2:31]

Participants

5

Reactant 4

HCID 15620607Glyoxylic acid, monohydrateHCID 167821003-Amino-4-fluorobenzamideHCID 594794353-Ethyl-4-fluorophenylboronic acidHCID 598380342-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Product 1

HCID 594794582-(5-Carbamoyl-2-fluorophenylamino)-2-(3-ethyl-4-fluorophenyl)acetic acidYield 48%

Procedure

95C was prepared in a procedure similar to that of 1A using 19B, 95B and glyoxylic acid monohydrate. Yield: 48%. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.19 (t, J=7.69 Hz, 3H) 2.65 (q, J=7.47 Hz, 2H) 5.18 (s, 1H) 6.98-7.11 (m, 3 H) 7.12-7.18 (m, 1H) 7.31-7.38 (m, 1H) 7.40-7.45 (m, 1H); LCMS: 335 (M+1).

Sources & evidence

ORD record
ord-e9737156df23478a85b71f8f5159c6ad
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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