Trifluoroacetic acid → (S)-2-((1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidin-2-carbonyl)oxy)acetic acid
Reaction equation
[N:1]1([C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[O:7].C([SiH](C(C)C)C(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:23]1[C:22]2[CH:21]([CH2:20][O:19][C:17]([N:1]3[CH2:5][CH2:4][CH2:3][C@H:2]3[C:6]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[O:18])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (S)-1-((9H-fluoren-9-yl)methyl) 2-(2-(tert-butoxy)-2-oxoethyl) pyrrolidine-1,2-dicarboxylate (Fmoc-Pro-HOGly-OtBu) (Compound SP631) (6.40 g, 14.2 mmol) in methylene chloride (29 mL) was mixed with triisopropylsilane (7.29 mL, 35.4 mmol) and trifluoroacetic acid (14.2 mL, 184 mmol) with stirring at room temperature, and the reaction mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford (S)-2-((1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidin-2-carbonyl)oxy)acetic acid (Fmoc-Pro-HOGly-OH) (Compound SP632) (5.6 g, 14.2 mmol, 100%).
Workup
- stirringthe reaction mixture was stirred at room temperature for 16 hours
- concentrationThe reaction solution was concentrated under reduced pressure
- customthe resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)
Sources & evidence
- ORD record
- ord-2a69fbcfa8c24e5d9f91f9dbdafdc4c1
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
Loading…