Trifluoroacetic acid → HCID 54673360, compound

HRID 509551Notes

Reaction equation

HRID 509551 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([C:23]1[C:28]([C:29]2[O:33][N:32]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[CH:30]=2)=[CH:27][C:26]([C:41]2[CH:46]=[CH:45][C:44]([S:47]([CH:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])=[CH:43][N:42]=2)=[CH:25][N:24]=1)C(=O)OC(C)(C)C)=O)(C)(C)C>C(Cl)Cl>[CH:50]([S:47]([C:44]1[CH:45]=[CH:46][C:41]([C:26]2[CH:27]=[C:28]([C:29]3[O:33][N:32]=[C:31]([C:34]4[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=4)[CH:30]=3)[C:23]([NH2:15])=[N:24][CH:25]=2)=[N:42][CH:43]=1)(=[O:48])=[O:49])([CH3:52])[CH3:51]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68088706HCID 68088706, compound

Product 1

HCID 54673360HCID 54673360, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL, 12.98 mmol) was added to a stirred solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(5-isopropylsulfonyl-2-pyridyl)-3-[3-(p-tolyl)isoxazol-5-yl]-2-pyridyl]carbamate (90 mg, 0.1418 mmol) in DCM (5 mL) and the reaction stirred at ambient temperature for 16 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The residue was redissolved in MeCN/water and passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a pale yellow solid (26 mg, 39% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.22 (d, J=6.8 Hz, 6H), 2.40 (s, 3H), 3.56 (sept, 1H), 7.05 (s, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.61 (s, 1H), 7.88 (d, J=8.1 Hz, 2H), 8.24-8.31 (m, 2H), 8.74 (d, J=2.2 Hz, 1H), 8.99 (d, 1H) and 9.02 (d, 1H) ppm; MS (ES+) 435.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. dissolutionThe residue was redissolved in MeCN/water
  4. customfreeze-dried

Sources & evidence

ORD record
ord-3a801e1c26da4d488b31e38632155c57
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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