Glyoxylic acid, monohydrate → 2-(4-(2-(3-((S)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

HRID 735595Notes

Reaction equation

HRID 735595 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]1[CH:20]=[C:21]([NH:25][C:26]([O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][C:32]=2[CH3:40])=[O:27])[CH:22]=[CH:23][CH:24]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:41][C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][CH:51]=1)[C:48]([N:52]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[N:47][CH:46]=[CH:45]2.O.[C:68]([OH:72])(=[O:71])[CH:69]=O>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]1[CH:20]=[C:21]([NH:25][C:26]([O:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH:69]([NH:41][C:42]3[CH:43]=[C:44]4[C:49](=[CH:50][CH:51]=3)[C:48]([N:52]([C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:54])[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[N:47][CH:46]=[CH:45]4)[C:68]([OH:72])=[O:71])=[CH:33][C:32]=2[CH3:40])=[O:27])[CH:22]=[CH:23][CH:24]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 57842792(S)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578429002-(4-(2-(3-((S)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acidYield 96%

Procedure

Using a procedure analogous to that used to prepare 2D, 34E (400 mg, 0.73 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 34F (670 mg, 96%) as a yellow foam. MS (ESI) m/z 697.15 (M+H)+.

Sources & evidence

ORD record
ord-eb553e92795645aa8471c743ccdf9e9d
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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