3-Aminobenzamide → 2-(4-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)-3-ethylphenyl)-2-(3-carbamoylphenylamino)acetic acid

HRID 735547Notes

Reaction equation

HRID 735547 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:23][C:24](=[O:39])[CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][C:29]=2[CH2:37][CH3:38])[CH:14]=[CH:15][C:16]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44]([NH2:46])=[O:45].O.[C:51]([OH:55])(=[O:54])[CH:52]=O>>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:23][C:24](=[O:39])[CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH:52]([NH:40][C:41]3[CH:49]=[CH:48][CH:47]=[C:43]([C:44](=[O:45])[NH2:46])[CH:42]=3)[C:51]([OH:55])=[O:54])=[CH:30][C:29]=2[CH2:37][CH3:38])[CH:14]=[CH:15][C:16]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 16453-AminobenzamideHCID 15620607Glyoxylic acid, monohydrateHCID 578428014-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)-3-ethylphenylboronic acid

Product 1

HCID 578428452-(4-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)-3-ethylphenyl)-2-(3-carbamoylphenylamino)acetic acid

Procedure

Using a procedure analogous to that used to prepare 2D, 21D (0.0.168 g, 0.300 mmol) was reacted with 3-aminobenzamide (0.041 g, 0.300 mmol) and glyoxylic acid monohydrate (0.028 g, 0.30 mmol) to give, after purification by reverse phase HPLC, 21E (134 mg, 63%) as a foam. MS (ESI) m/z 709.52 (M+H)+.

Workup

  1. customto give
  2. customafter purification by reverse phase HPLC, 21E (134 mg, 63%) as a foam

Sources & evidence

ORD record
ord-e97f920bafa14181b8511b12491026ea
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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