Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-((tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenyl)acetic acid

HRID 735660Notes

Reaction equation

HRID 735660 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][C:23]=2[Cl:31])=[O:18])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[C:39]([N:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:38][CH:37]=[CH:36]2.O.[C:59]([OH:63])(=[O:62])[CH:60]=O>>[C:54]([O:53][C:51]([N:43]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[C:39]1[C:40]2[C:35](=[CH:34][C:33]([NH:32][CH:60]([C:25]3[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][O:19][C:17](=[O:18])[NH:16][C:12]4[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:11]=4)=[C:23]([Cl:31])[CH:24]=3)[C:59]([OH:63])=[O:62])=[CH:42][CH:41]=2)[CH:36]=[CH:37][N:38]=1)=[O:52])([CH3:57])([CH3:56])[CH3:55]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578427284-(2-(3-((Tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578427172-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-((tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenyl)acetic acidYield 86%

Procedure

Using a procedure analogous to that used to prepare 2D, 61E (350 mg, 0.781 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 61F (547 mg, 86%) as an oil. MS (ESI) m/z 822.0 (M+2 H)+.

Sources & evidence

ORD record
ord-5e4efb09d6e847088dc490542e79ddee
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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