Trifluoroacetic acid → HCID 11718248, compound

HRID 870354Notes

Reaction equation

HRID 870354 reaction equation
C(OC(=O)[N:7]([CH2:32][CH:33]=[CH2:34])[C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH3:19])[CH:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH2:32]([NH:7][C@H:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([N:18]([CH3:19])[S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:30])[CH3:31])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[CH:33]=[CH2:34]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68912510HCID 68912510, compound

Product 1

HCID 11718248HCID 11718248, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl-{(S)-6-[(4-isopropyl-benzenesulfonyl)-methyl-amino]-1,2,3,4-tetrahydronaphthalen-2-yl}-carbamic acid tert-butyl ester (672 mg, 1.35 mmol) was dissolved in dichloromethane (30 ml). Trifluoroacetic acid (1 ml) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. Ethyl acetate (100 ml) was added and extracted with NaOH (2M). The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 1.05 g of crude product. The crude product was dissolved in ethyl acetate (20 ml) and the precipitate was collected to yield the desired compound (270 mg, 50%). The mother liquid was reduced in vacuo to yield an oil (840 mg, 54% purity).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionEthyl acetate (100 ml) was added
  3. extractionextracted with NaOH (2M)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield 1.05 g of crude product
  8. customthe precipitate was collected

Sources & evidence

ORD record
ord-a6c4d510fbf64df28aab6537e8c77990
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…