Trifluoroacetic acid → HCID 178495718, compound

HRID 548748Notes

Reaction equation

HRID 548748 reaction equation
FC(F)(F)C(O)=O.[O:8]=[S:9]1(=[O:48])[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:21]3[CH:22]=[C:23]([C:33]([NH:35][C:36]4[CH:40]=[CH:39][N:38](C(OC(C)(C)C)=O)[N:37]=4)=[O:34])[CH:24]=[C:25]([O:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])[CH:26]=3)=[CH:19][C:14]=2[O:13][CH2:12][CH2:11][NH:10]1>C(Cl)Cl>[O:48]=[S:9]1(=[O:8])[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:21]3[CH:22]=[C:23]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])[CH:26]=3)[C:33]([NH:35][C:36]3[CH:40]=[CH:39][NH:38][N:37]=3)=[O:34])=[CH:19][C:14]=2[O:13][CH2:12][CH2:11][NH:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57663157HCID 57663157, compound

Product 1

HCID 178495718HCID 178495718, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of 1,1-dimethylethyl 3-{[(3-[(1,1-dioxido-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl)oxy]-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}phenyl)carbonyl]amino}-1H-pyrazole-1-carboxylate (47 mg, 0.08 mmol) in DCM (8 mL) and stirred at RT for 2 hours. The solvent was removed in vacuo, DCM (20 mL) added and the mixture washed with water (20 mL), a saturated solution of sodium bicarbonate (20 mL), brine (20 mL), dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a white foam (39 mg).

Workup

  1. customThe solvent was removed in vacuo, DCM (20 mL)
  2. additionadded
  3. washthe mixture washed with water (20 mL)
  4. dry with materiala saturated solution of sodium bicarbonate (20 mL), brine (20 mL), dried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-efd9fcad48e045a0b124852366d6a52d
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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