Trifluoroacetic acid → 3-Aminomethyl-5-methyl-hexanoic acid 1-ethyloxycarbonyloxy-ethyl ester TFA salt
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:10][C:11]([O:13][CH:14]([O:16][C:17](=[O:33])[CH2:18][CH:19]([CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH3:15])=[O:12])[CH3:9]>C(Cl)Cl>[OH:5][C:3]([C:2]([F:7])([F:6])[F:1])=[O:4].[CH2:8]([O:10][C:11]([O:13][CH:14]([O:16][C:17](=[O:33])[CH2:18][CH:19]([CH2:24][NH2:25])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH3:15])=[O:12])[CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (6.5 mL) was added to a solution of compound 4 (0.407 g, 1.08 mmol) and CH2Cl2 (2.85 mL) in an ice water bath, and the solution was maintained in the ice water bath for 30 minutes. The solution was warmed to room temperature and stirred for another 4.5 hours. The reaction solution was then concentrated and dried to give 0.50 g of 3-Aminomethyl-5-methyl-hexanoic acid 1-ethyloxycarbonyloxy-ethyl ester TFA salt 5 (Yield: 99%). 1HNMR (CDCl3, 500 MHz) δ 0.87˜0.91 (m, 6H), 1.23˜1.39 (m, 6H), 1.51 (6rs, 3H), 1.61 (S, 1H), 2.20˜2.38 (m, 1H), 2.40˜2.61 (m, 2H), 2.98˜3.21 (m, 2H), 4.2 (br s, 2H), 6.75 (br s 1H), 7.51˜7.80 (br s, 2H), 9.35˜9.80 (br s, 1H); 13C NMR (CDCl3, 125 MHz) δ13.86, 13.87, 19.16, 19.19, 21.70, 21.74, 22.38, 22.40, 24.83, 30.95, 31.02, 36.48, 36.69, 41.07, 41.32, 44.25, 44.36, 64.82, 91.41, 91.45, 153.38, 153.40, 171.87, 172.08.
Workup
- concentrationThe reaction solution was then concentrated
- customdried
Sources & evidence
- ORD record
- ord-020db99032ba41e1b93512e66acd143c
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879906B2
Reaction notes
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