Trifluoroacetic acid → Fmoc-N-methyl-S-tert-butylthio-L-cysteine
Reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[C:15]([S:19][S:20][CH2:21][C@H:22]1[C:26](=[O:27])[O:25][CH2:24][N:23]1[C:28]([O:30][CH2:31][CH:32]1[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[CH:34]1[C:33]2[CH:32]([CH2:31][O:30][C:28]([N:23]([CH3:24])[C@@H:22]([CH2:21][S:20][S:19][C:15]([CH3:17])([CH3:16])[CH3:18])[C:26]([OH:27])=[O:25])=[O:29])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylsilane (6.04 ml, 37.8 mmol) and trifluoroacetic acid (9 ml) were added to a solution of (R)-(9H-fluoren-9-yl)methyl 4-((tert-butyldisulfanyl)methyl)-5-oxooxazolidine-3-carboxylate (Compound 2b-B) (1.68 g, 3.78 mmol) in dichloromethane (18 ml), and the mixture was stirred at room temperature for one day. 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=70/30→20/80→0/100) to afford (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(tert-butyldisulfanyl)propanoic acid (Compound 2c-B) (1.22 g, 72%).
Workup
- concentrationThe reaction mixture was then concentrated under reduced pressure
- customthe residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→20/80→0/100)
Sources & evidence
- ORD record
- ord-a2e5a1d8fdf443a6a1a0a1366ccbf022
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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