Triethylamine → Methyl 2-{[2-(trans-crotonylamino)-5-methylbenzyl]-(4-methoxybenzenesulfonyl) amino}acrylate

HRID 1420612Notes

Reaction equation

HRID 1420612 reaction equation
O[CH2:2][CH:3]([N:8]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[NH2:17])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:36](Cl)(=[O:40])/[CH:37]=[CH:38]/[CH3:39]>C(Cl)Cl>[C:36]([NH:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH2:9][N:8]([S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:19])=[O:20])[C:3](=[CH2:2])[C:4]([O:6][CH3:7])=[O:5])(=[O:40])/[CH:37]=[CH:38]/[CH3:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 643131trans-Crotonyl chlorideHCID 18612905Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate

Product 1

HCID 86755438Methyl 2-{[2-(trans-crotonylamino)-5-methylbenzyl]-(4-methoxybenzenesulfonyl) amino}acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described for Reference Examples 181 and 182, a mixture of 1.41 g (3.455 mmol) of methyl 3-hydroxy-2-[-(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate, 1.75 g (17.3 mmol) of triethylamine and 0.809 ml of trans-crotonyl chloride in 15 ml of CH2Cl2 was stirred overnight to give 1.52 g of methyl 2-{[2-(trans-crotonylamino)-5-methylbenzyl]-(4-methoxybenzenesulfonyl) amino}acrylate as a brown oil; Mass spectrum (ES) 459.4 (M+H).

Sources & evidence

ORD record
ord-9841ab28fc15418eb8c9c8dfb4f49876
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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