5-(2-tert-Butoxycarbonyl-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester → 5-(2-tert-Butoxycarbonyl-ethyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

HRID 583357Notes

Reaction equation

HRID 583357 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[C:6]([CH3:19])[C:5]=1[N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21]>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH:7]=[C:6]([CH3:19])[C:5]=1[N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21]

Participants

4

Reactant 1

HCID 700548965-(2-tert-Butoxycarbonyl-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

Product 1

HCID 700529905-(2-tert-Butoxycarbonyl-ethyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl esterYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 340 mg (0.71 mmol) of the product of Example 203 and 35 mg of 10% palladium on carbon in 15 ml of ethanol was hydrogenated on a Parr shaker for 2 hr. The resulting mixture was filtered through Celite and Magnesol to provide 325 mg (95%) of the desired product as a colorless gum. Electrospray Mass Spec 478(M+H).

Workup

  1. filtrationThe resulting mixture was filtered through Celite and Magnesol

Sources & evidence

ORD record
ord-58a23ff48de740e38147d71fd2deb5cb
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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