Glyoxylic acid, monohydrate → HCID 57842711, compound

HRID 735673Notes

Reaction equation

HRID 735673 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][C:27]=2[CH3:35])=[O:22])[CH:17]=[CH:18][CH:19]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[C:43]([N:47]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[N:42][CH:41]=[CH:40]2.O.[C:63]([OH:67])(=[O:66])[CH:64]=O>>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH:64]([NH:36][C:37]3[CH:38]=[C:39]4[C:44](=[CH:45][CH:46]=3)[C:43]([N:47]([C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])=[N:42][CH:41]=[CH:40]4)[C:63]([OH:67])=[O:66])=[CH:28][C:27]=2[CH3:35])=[O:22])[CH:17]=[CH:18][CH:19]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 57842816HCID 57842816, compoundHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 57842711HCID 57842711, compoundYield 95%

Procedure

Using a procedure analogous to that used to prepare 2D, 64D (175 mg, 0.37 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 65A (300 mg, 95%) as an oil. MS (ESI) m/z 848.5 (M+H)+.

Sources & evidence

ORD record
ord-189b4b30ccb44bb197bd87f9bdafe129
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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