Trifluoroacetic acid → (S)-4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoic acid
Reaction equation
C(N=C=NC(C)C)(C)C.[C:10]1([CH2:16][SH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O:22][C:23](=[O:36])[C@@H:24]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[CH2:25][C:26](O)=[O:27])(C)(C)C.C(O)(=O)CCC=C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:16]([S:17][C:26](=[O:27])[CH2:25][C@H:24]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[C:23]([OH:36])=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
DIC (N,N′-diisopropylcarbodiimide) (2.41 ml, 15.5 mmol), DMAP (N,N-dimethylaminopyridine) (315 mg, 2.58 mmol) and phenylmethanethiol (1.82 ml, 15.5 mmol) were added to a solution of the mixed crude product A (2.51 g, 12.9 mmol) of (S)-4-(tert-butoxy)-4-oxo-3-(pent-4-enamido)butanoic acid (Compound 1b-I) and pent-4-enoic acid (1:0.8) in CH2Cl2 (35 ml), and the mixture was stirred at room temperature for 4 hours. TFA (21 ml) was then added to the reaction mixture, which was stirred at room temperature for 9.5 hours. The reaction mixture was then concentrated under reduced pressure, and the resulting residue was reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=80/20→40/60) to afford (S)-4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoic acid (Compound 1f-ID) (1.65 g, 74%).
Workup
- stirringwas stirred at room temperature for 9.5 hours
- concentrationThe reaction mixture was then concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5e64cc598cfc403b903f5a3a8bf9cd5f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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