Lithium Hydroxide → (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine
Reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)=[O:4].[Li+].[OH-]>CO.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)([OH:4])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (4S)-2-(4-methoxycarbonyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (prepared in a manner analogous to that described in Method D2a; 0.035 g, 0.097 mmol) in a mixture of MeOH (1.5 mL) and H2O (1.5 mL) was added LiOH (0.016 g, 0.39 mmol). The resulting mixture was stirred for 2 d at room temp., then was concentrated under reduced pressure. The residue was adjusted to pH 1 with a 1% HCl solution, then extracted with EtOAc (4×10 mL). The combined organic layers were sequentially washed with H2O (15 mL), a saturated NaCl solution (15 mL), and dried (Na2SO4). Concentration under reduced pressure gave (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (0.034 g, 100%): TLC (40% EtOAc/hex) Rf 0.08. This material was used in the next step without further purification.
Workup
- concentrationwas concentrated under reduced pressure
- extractionextracted with EtOAc (4×10 mL)
- washThe combined organic layers were sequentially washed with H2O (15 mL)
- dry with materiala saturated NaCl solution (15 mL), and dried (Na2SO4)
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-08191173ef1345d48ffc6d55a539a27c
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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