Trifluoroacetic acid → (S)-4-(methylthio)-4-oxo-2-(pent-4-enamido)butanoic acid

HRID 1482183Notes

Reaction equation

HRID 1482183 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9][C:10](=[O:27])[CH2:11][C@H:12]([NH:20][C:21](=[O:26])[CH2:22][CH2:23][CH:24]=[CH2:25])[C:13]([O:15]C(C)(C)C)=[O:14]>ClCCl>[CH3:8][S:9][C:10](=[O:27])[CH2:11][C@H:12]([NH:20][C:21](=[O:26])[CH2:22][CH2:23][CH:24]=[CH2:25])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89668258(S)-tert-butyl 4-(methylthio)-4-oxo-2-(pent-4-enamido)butanoate

Product 1

HCID 89668301(S)-4-(methylthio)-4-oxo-2-(pent-4-enamido)butanoic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.684 ml, 9.20 mmol) was added to a solution of (S)-tert-butyl 4-(methylthio)-4-oxo-2-(pent-4-enamido)butanoate (Compound 1e-IA, 69.3 mg, 0.23 mmol) in dichloromethane (1.2 ml), and the mixture was stirred at room temperature for 6.5 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40) to afford (S)-4-(methylthio)-4-oxo-2-(pent-4-enamido)butanoic acid (Compound 1f-IA) (46.9 mg, 83%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40)

Sources & evidence

ORD record
ord-54e407792ddb453888b4137ff6a38345
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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