Trifluoroacetic acid → 3-Methyl-2-(2-phenyl-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-sulfonylmethyl)-butyric Acid
Reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH2:10][NH:11][CH2:12][CH2:13][C:14]=3[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:20][C:21](=[O:31])[CH:22]([CH2:26][S:27](Cl)(=[O:29])=[O:28])[CH:23]([CH3:25])[CH3:24])(C)(C)C.C(N(CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:24][CH:23]([CH3:25])[CH:22]([CH2:26][S:27]([N:11]1[CH2:12][CH2:13][C:14]2[N:15]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][C:9]=2[CH2:10]1)(=[O:29])=[O:28])[C:21]([OH:31])=[O:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Phenyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (0.11 g) was added to a solution of 2-chlorosulfonylmethyl-3-methyl-butyric acid tert-butyl ester (0.14 g) and triethylamine (0.3 ml) in DCM (20 ml) at room temperature. The solution was stirred for 2 h, then TFA (5 ml) was added and the mixture stirred for 1 h. The mixture was evaporated in vacuo and the residue partitioned between diethyl ether (10 ml) and saturated sodium bicarbonate (30 ml). The aqueous layer was acidified with citric acid to pH 5 and extracted with ethyl acetate (3×20 ml). The solvent was dried (MgSO4) and evaporated to give the title compound as pale yellow solid (0.15 g).
Workup
- stirringthe mixture stirred for 1 h
- customThe mixture was evaporated in vacuo
- customthe residue partitioned between diethyl ether (10 ml) and saturated sodium bicarbonate (30 ml)
- extractionextracted with ethyl acetate (3×20 ml)
- dry with materialThe solvent was dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-a8fdb5747e5b42ac8c9081f81734dedb
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506773B2
Reaction notes
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