Trifluoroacetic acid → HCID 9859131, compound

HRID 844533Notes

Reaction equation

HRID 844533 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13]([N:15]1[CH2:19][CH:18]=[CH:17][C@H:16]1[C:20]#[N:21])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([N:15]1[CH2:19][CH:18]=[CH:17][C@H:16]1[C:20]#[N:21])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86583778HCID 86583778, compound

Product 1

HCID 9859131HCID 9859131, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(140 mg, 0.46 mmol) of (3) was dissolved in 0.5 ml of dichloromethane and the mixture was cooled to 0° C. 0.5 ml of trifluoroacetic acid was added and the reaction mixture was stirred at 0° C. for 1 hour. The solvent was evaporated and the crude product was purified by preparative HPLC, using acetonitrile/water as the eluent. Fractions containing the product were collected and the solvent was evaporated, to afford 25 mg of the title compound (1) as the trifluoroacetic acid salt. Oil, 17% yield. 1H-NMR (MeOH, 200 MHz) δ: 1.20 (s, 9H); 4.08 (s, 1H); 4.46-4.70 (m, 2H); 5.56-5.62 (m, 1H); 5.95-6.02 (m, 1H); 6.22-6.29 (m, 1H). LC-MS, m/z: 208.4 (M+1)

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by preparative HPLC
  3. additionFractions containing the product
  4. customwere collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-08d67e2f24b3486abddc5134778f6465
Source dataset
uspto-grants-2002_04
Patent number
US06380398B2

Reaction notes

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