2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester → 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)amino]-3-methylbutyric acid

HRID 1006089Notes

Reaction equation

HRID 1006089 reaction equation
C([O:8][C:9](=[O:39])[C@H:10]([N:14]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]2[O:36][CH2:37][O:38][C:32]=2[CH:31]=1)[S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH3:26])=[C:20]([CH3:27])[C:19]=1[CH3:28])(=[O:17])=[O:16])[CH:11]([CH3:13])[CH3:12])C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[CH2:37]1[O:36][C:33]2[CH:34]=[CH:35][C:30]([CH2:29][N:14]([S:15]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH3:26])=[C:20]([CH3:27])[C:19]=3[CH3:28])(=[O:17])=[O:16])[C@H:10]([CH:11]([CH3:13])[CH3:12])[C:9]([OH:39])=[O:8])=[CH:31][C:32]=2[O:38]1

Participants

4

Reactant 1

HCID 111804222(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester

Product 1

HCID 114311912(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)amino]-3-methylbutyric acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester (4.7 g, 8.49 mmol) in a 4:1 mixture of ethanol/tetrahydrofuran (40 mL) was added 10% Pd/C (0.15 g). The reaction mixture was placed under a hydrogen balloon. After 3 h, the reaction mixture was filtered through Celite and the Celite cake was washed with ethanol. The filtrate was concentrated to give of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyric acid (3.9 g) as a white foam.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. washthe Celite cake was washed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-528ce1ef8a7b4cce99a621d84e4225cb
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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