Glyoxylic acid, monohydrate → 2-(4-(2-(3-((Tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylcarbamoyloxy)ethyl)-3-ethylphenyl)-2-(5-carbamoyl-2-fluorophenylamino)acetic acid

HRID 735619Notes

Reaction equation

HRID 735619 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([O:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][C:30]=2[CH2:38][CH3:39])=[O:25])[CH:14]=[CH:15][C:16]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][C:49]=1[F:50])[C:44]([NH2:46])=[O:45].O.[C:52]([OH:56])(=[O:55])[CH:53]=O>>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([O:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH:53]([NH:40][C:41]3[CH:42]=[C:43]([C:44](=[O:45])[NH2:46])[CH:47]=[CH:48][C:49]=3[F:50])[C:52]([OH:56])=[O:55])=[CH:31][C:30]=2[CH2:38][CH3:39])=[O:25])[CH:14]=[CH:15][C:16]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 167821003-Amino-4-fluorobenzamideHCID 578426934-(2-(3-((Tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylcarbamoyloxy)ethyl)-3-ethylphenylboronic acid

Product 1

HCID 578427252-(4-(2-(3-((Tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylcarbamoyloxy)ethyl)-3-ethylphenyl)-2-(5-carbamoyl-2-fluorophenylamino)acetic acidYield 62%

Procedure

Using a procedure analogous to that used to prepare 2D, 43B (362 mg, 0.65 mmol) was reacted with 3-amino-4-fluorobenzamide and glyoxylic acid monohydrate to afford 43C (296 mg, 62%) as a yellow oil. MS (ESI) m/z 729.3 (M+H)+.

Sources & evidence

ORD record
ord-8db93195244a4f1e80b34d6f50576ea6
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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