Water → (4S)-2-(4-carbamoyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:13][S:12]2)=[C:6]([CH3:24])[CH:5]=1)(O)=[O:2].C(C1NC=CN=1)(C1[NH:28]C=CN=1)=O.O>C(Cl)Cl.N>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:13][S:12]2)=[C:6]([CH3:24])[CH:5]=1)(=[O:2])[NH2:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (0.035 g, 0.10 mmol) in CH2Cl2 (5 mL) was added carbonyl diimidazole (0.047 g, 0.29 mmol). The mixture was allowed to stir at room temp. for 2 h, then anh NH3 (approximately 30 drops) was condensed into the solution at −78° C. The resulting mixture was warmed to room temp. overnight, then treated with H2O (20 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL), sequentially washed with H2O (20 mL) and a saturated NaCl solution (20 mL), dried Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (40% EtOAc/hexane) to give (4S)-2-(4-carbamoyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine as a white solid (0.027 g, 73%): mp 130-131° C.
Workup
- customcondensed into the solution at −78° C
- temperatureThe resulting mixture was warmed to room temp. overnight
- extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
- washsequentially washed with H2O (20 mL)
- concentrationa saturated NaCl solution (20 mL), dried Na2SO4), and concentrated under reduced pressure
- customThe residue was purified by flash chromatography (40% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-e8f8be88f928488492321ae3bc8a2fbc
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
Loading…