Trifluoroacetic acid → 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionic acid

HRID 1006124Notes

Reaction equation

HRID 1006124 reaction equation
[CH2:1]1[O:38][C:37]2[CH:36]=[CH:35][C:5]([CH2:6][N:7]([S:22]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([O:32][CH3:33])=[CH:27][C:26]=3[CH3:34])(=[O:24])=[O:23])[C@H:8]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][C:3]=2[O:2]1.FC(F)(F)C(O)=O>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:1]1[O:38][C:37]2[CH:36]=[CH:35][C:5]([CH2:6][N:7]([S:22]([C:25]3[C:26]([CH3:34])=[CH:27][C:28]([O:32][CH3:33])=[CH:29][C:30]=3[CH3:31])(=[O:23])=[O:24])[C@H:8]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18337582tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate

Product 1

HCID 183375492(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate (1.37 g, 2 mmol) in 20% trifluoracetic acid-methylene chloride (15 ml) was stirred for 1 hour. Extra trifluoroacetic acid (0.5 ml) was added and stirring continued for two hours. The material was then condensed on the rotary evaporator and the residue was taken up in toluene (40 ml) and again condensed. This procedure was repeated twice (2×40 ml toluene, to remove traces of trifluoracetic acid) to provide 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionic acid as a tan green foamy solid (1.02 g).

Workup

  1. customcondensed
  2. customon the rotary evaporator
  3. customagain condensed
  4. custom(2×40 ml toluene, to remove traces of trifluoracetic acid)

Sources & evidence

ORD record
ord-e9e478ebf79248f3adb0dd61188b23be
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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