Benzoyl chloride → 2-[(2-Benzoylamino-benzyl)-(4-methoxy-benzenesulfonyl)-amino]-acrylic acid methyl ester

HRID 1180557Notes

Reaction equation

HRID 1180557 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]([CH2:11]O)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:10][O:9][C:7](=[O:8])[C:6]([N:5]([CH2:4][C:3]1[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=1[NH:1][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:15])=[O:14])=[CH2:11]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18612758Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate

Product 1

HCID 186130262-[(2-Benzoylamino-benzyl)-(4-methoxy-benzenesulfonyl)-amino]-acrylic acid methyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 33 was followed using the product from Example 32 (500 mg, 1.268 mmol), triethylamine (0.884 ml, 6.34 mmol), and benzoyl chloride (0.324 ml, 2.79 mmol) in methylene chloride (60 ml) to give 620 mg (100%) of the product.

Sources & evidence

ORD record
ord-5ae80c2edc15446bbdc25c19353a49a5
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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