3-Aminobenzamide → 2-(4-(2-(3-((R)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(3-carbamoylphenylamino)acetic acid

HRID 735616Notes

Reaction equation

HRID 735616 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]([CH:48]=[CH:49][CH:50]=1)[C:45]([NH2:47])=[O:46].O.[C:52]([OH:56])(=[O:55])[CH:53]=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:53]([NH:41][C:42]3[CH:50]=[CH:49][CH:48]=[C:44]([C:45](=[O:46])[NH2:47])[CH:43]=3)[C:52]([OH:56])=[O:55])=[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 16453-AminobenzamideHCID 15620607Glyoxylic acid, monohydrateHCID 57842846(R)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid

Product 1

HCID 578428212-(4-(2-(3-((R)-1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(3-carbamoylphenylamino)acetic acidYield 44%

Procedure

Using a procedure analogous to that used to prepare 2D, 39E (200 mg, 0.36 mmol) was reacted with 3-aminobenzamide and glyoxylic acid monohydrate to afford 41A (232 mg, 44%) as a brown oil. MS (ESI) m/z 697.4 (M+H)+.

Sources & evidence

ORD record
ord-28c791d9cd9f4cbd83388e284be6152b
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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