Trifluoroacetic acid → (3RS)-3-[N-((1-Naphthyloxy)Acetyl)Valinyl]Amino-5-Fluoro-4-Oxopentanoic Acid
Reaction equation
[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][F:34])[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][F:34])[CH2:24][C:25]([OH:27])=[O:26])=[O:21])[CH:17]([CH3:18])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3RS)-3-[N-((1-naphthyloxy)acetyl)valinyl]amino-5-fluoro-4-oxopentanoic acid, tert-butyl ester (0.113 g, 0.23 mmol) in CH2Cl2(2.0 mL)-anisole(0.5 mL) at room temperature under nitrogen was added trifluoroacetic acid (1.0 mL). The resulting clear solution was stirred at room temperature for 1 hr, evaporated to dryness and chased with toluene-CH2Cl2 (1:1). The residue was purified by flash chromatography on silica gel eluting with AcOH-MeOH-CH2Cl2 (0.5:2:100) to give the title compound (0.069 g, 69%) as a white solid. TLC(AcOH-MeOH-CH2Cl2; 1:1:20) Rf=0.38. MS(ES) for C22H25FN2O6 (MW 432.45): positive 433(M+NH); negative 431(M−H). 1H NMR (CD3OD): δ 8.32–8.29 (m, 1H), 7.82–7.79 (m, 1H), 7.49–7.46 (m, 3H), 7.38–7.32 (m, 1H), 6.88 (d, 1H, J=7.7 Hz), 4.78–4.73 (m, 2H), 4.55–4.26 (m, 2H), 2.82–2.76 (m, 2H), 2.16–2.03 (m, 1H), 0.94–0.85 (m, 6H).
Workup
- customevaporated to dryness
- customThe residue was purified by flash chromatography on silica gel eluting with AcOH-MeOH-CH2Cl2 (0.5:2:100)
Sources & evidence
- ORD record
- ord-89590ad7c21e4437963e0a83a6fd706e
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157430B2
Reaction notes
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