Glyoxylic acid, monohydrate → 2-(1-(bis(tert-Butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-((tert-butoxycarbonyl(methyl)amino)methyl)-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenyl)acetic acid

HRID 735533Notes

Reaction equation

HRID 735533 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:22][C:23](=[O:36])[CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=2)[CH:14]=[CH:15][C:16]=1[S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:37][C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[C:44]([N:48]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[N:43][CH:42]=[CH:41]2.O.[C:64]([OH:68])(=[O:67])[CH:65]=O>>[C:59]([O:58][C:56]([N:48]([C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[C:44]1[C:45]2[C:40](=[CH:39][C:38]([NH:37][CH:65]([C:30]3[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][CH2:24][C:23]([NH:22][C:13]4[CH:14]=[CH:15][C:16]([S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[C:11]([CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:9])[CH:12]=4)=[O:36])=[CH:28][CH:29]=3)[C:64]([OH:68])=[O:67])=[CH:47][CH:46]=2)[CH:41]=[CH:42][N:43]=1)=[O:57])([CH3:62])([CH3:61])[CH3:60]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578429044-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578427082-(1-(bis(tert-Butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-((tert-butoxycarbonyl(methyl)amino)methyl)-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenyl)acetic acid

Procedure

Using a procedure analogous to that used to prepare 2D, 17D (0.130 g, 0.25 mmol) was reacted with Intermediate 1 (0.090 g, 0.25 mmol) and glyoxylic acid monohydrate (0.027 g, 0.29 mmol) to give, after purification by reverse phase HPLC, 17E (109 mg, 49%). MS (ESI) m/z 890.1 (M+H)+.

Workup

  1. customto give
  2. customafter purification by reverse phase HPLC, 17E (109 mg, 49%)

Sources & evidence

ORD record
ord-5a25074e37de4ecf93c3dbcb8a13c8d5
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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