Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetic acid

HRID 735626Notes

Reaction equation

HRID 735626 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14](B(O)O)=[CH:13][C:12]=1[CH3:21])(C(C)(C)C)(C)C.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([N:33]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[N:28][CH:27]=[CH:26]2.O.[C:49]([OH:53])(=[O:52])[CH:50]=O>>[C:44]([O:43][C:41]([N:33]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[C:29]1[C:30]2[C:25](=[CH:24][C:23]([NH:22][CH:50]([C:14]3[CH:13]=[C:12]([CH3:21])[C:11]([CH2:10][CH2:9][OH:8])=[C:16]([CH3:17])[CH:15]=3)[C:49]([OH:53])=[O:52])=[CH:32][CH:31]=2)[CH:26]=[CH:27][N:28]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578425504-(2-(Tert-butyldimethylsilyloxy)ethyl)-3,5-dimethylphenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578427352-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetic acidYield 39%

Procedure

Using a procedure analogous to that used to prepare 2D, 50B (1.43 g, 4.6 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 50C (1.1 g, 39%) as an orange solid. MS (ESI) m/z 566.6 (M+H)+.

Sources & evidence

ORD record
ord-5ffcc14246f94e7899cf9bd1170cd1aa
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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