Trifluoroacetic acid → HCID 131728637, compound

HRID 1361047Notes

Reaction equation

HRID 1361047 reaction equation
[CH3:1][CH:2]([CH3:27])[CH:3]([O:9][C:10](=[O:26])[CH2:11][CH:12]([CH2:17][NH:18]C(OC(C)(C)C)=O)[CH2:13][CH:14]([CH3:16])[CH3:15])[O:4][C:5](=[O:8])[CH2:6][CH3:7].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(Cl)Cl>[OH:32][C:30]([C:29]([F:34])([F:33])[F:28])=[O:31].[CH3:27][CH:2]([CH3:1])[CH:3]([O:9][C:10](=[O:26])[CH2:11][CH:12]([CH2:17][NH2:18])[CH2:13][CH:14]([CH3:15])[CH3:16])[O:4][C:5](=[O:8])[CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72369228HCID 72369228, compound

Product 1

HCID 131728637HCID 131728637, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. temperaturemaintained for 30 minutes
  2. concentrationAfter concentrating
  3. customdrying

Sources & evidence

ORD record
ord-1434cd66acbe4ffbad41e34905060ac1
Source dataset
uspto-grants-2011_02
Patent number
US07879906B2

Reaction notes

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