Trifluoroacetic acid → HCID 131728637, compound

Participants

Reaction Steps

Compound 18 (0.196 g, 0.51 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (3.25 mL) was added in an ice water bath and maintained for 30 minutes. The solution was then warmed to room temperature and stirred for 5 hours. After concentrating and drying, 3-aminomethyl-5-methyl-hexanoic acid 2-methyl-1-propionyloxy-propyl ester TFA salt 19 (0.194 g) was obtained with a yield of 95%. 1HNMR (CD3OD, 500 MHz) δ0.88-0.92 (m, 6H), 0.94 (d, J=6.5 Hz, 3H), 1.08 (t, J=7.5 Hz, 2H), 1.20-1.28 (m, 2H), 1.60-1.69 (m, 1H), 1.95-2.02 (m, 1H), 2.16-2.23 (m, 1H), 2.29-2.46 (m, 3H), 2.89-2.98 (m, 2H), 3.27 (s, 1H), 6.59 (d, J=5 Hz, 1H); 13CNMR (CDCl3, 125 MHz) δ9.29, 9.31, 16.74, 16.84, 16.86, 22.58, 22.59, 23.25, 23.27, 23.31, 26.28, 26.32, 28.28, 32.83, 32.90, 32.95, 36.85, 36.93, 37.28, 41.80, 41.89, 42.24, 44.31, 44.34, 44.71, 49.66, 94.54, 94.57, 172.16, 172.18, 174.46. LC/MS: ESI positive mode (M+H): 288.30.

Provenance & Evidence