Trifluoroacetic acid → HCID 131728638, compound

HRID 1361048Notes

Reaction equation

HRID 1361048 reaction equation
[C:1]([O:6][CH:7]([O:10][C:11](=[O:27])[CH2:12][CH:13]([CH2:18][NH:19]C(OC(C)(C)C)=O)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH3:9])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[OH:34][C:28]([C:30]([F:33])([F:32])[F:31])=[O:29].[C:1]([O:6][CH:7]([O:10][C:11](=[O:27])[CH2:12][CH:13]([CH2:18][NH2:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH3:9])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72369230HCID 72369230, compound

Product 1

HCID 131728638HCID 131728638, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 24 (0.3 g, 0.77 mmol) was dissolved in CH2Cl2 (5 mL) and TFA (4.5 mL) was added and maintained in an ice water bath for 30 minutes. The solution was then warmed to room temperature and stirred for 5 hours. After concentrating and drying, 0.25 g of 3-aminomethyl-5-methyl-hexanoic acid 1-isobutyryloxy-propyl ester TFA salt 25 was obtained (Yield: 80%). 1HNMR (CDCl3, 500 MHz) δ0.87-0.95 (m, 6H), 1.15-1.65 (m, 4H), 1.18-1.28 (m, 2H), 1.52-1.67 (m, 1H), 1.71-1.82 (m, 2H), 2.18-2.31 (m, 1H), 2.39-2.46 (m, 1H), 2.51-2.62 (m, 2H), 3.02 (br s, 1H), 3.19 (br s, 1H), 6.89 (t, J=5.5 Hz, 1H), 7.48 (br s, 2H); 13CNMR (CDCl3, 125 MHz) δ 7.29, 7.35, 14.69, 18.39, 18.42, 18.48, 18.52, 21.70, 21.73, 22.43, 24.90, 26.18, 31.05, 31.13, 33.93, 36.92, 37.08, 41.26, 41.47, 44.73, 44.79, 66.05, 91.73, 91.83, 172.58, 172.69, 176.43.

Workup

  1. temperaturemaintained in an ice water bath for 30 minutes
  2. concentrationAfter concentrating
  3. customdrying

Sources & evidence

ORD record
ord-fafdf2acc3db47cfb6bbde762656feb7
Source dataset
uspto-grants-2011_02
Patent number
US07879906B2

Reaction notes

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