Trifluoroacetic acid → HCID 178495717, compound

HRID 548743Notes

Reaction equation

HRID 548743 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:15][CH2:14][O:13][C:12]2[CH:16]=[C:17]([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:18]=[CH:19][C:11]=2[S:10]1(=[O:49])=[O:48]>C(Cl)Cl>[CH3:8][N:9]1[CH2:15][CH2:14][O:13][C:12]2[CH:16]=[C:17]([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:18]=[CH:19][C:11]=2[S:10]1(=[O:49])=[O:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576631951,1-dimethylethyl 3-{[(3-[(2-methyl-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

Product 1

HCID 178495717HCID 178495717, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of 1,1-dimethylethyl 3-{[(3-[(2-methyl-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 (50 mg, 0.08 mmol) in DCM (8 mL) and stirred at RT for 2 hours. The solvent was removed in vacuo and DCM (20 mL). The mixture was 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 (31 mg). 1H NMR δ (CDCl3): 1.33 (d, 3H), 2.80 (s, 3H), 3.40 (s, 3H), 3.51-3.61 (m, 2H), 3.71-3.73 (m, 2H), 4.17-4.22 (m, 2H), 4.57-4.65 (m, 1H), 6.72-6.74 (m, 1H), 6.79-6.84 (m, 2H), 6.86 (s, 1H), 7.20 (s, 1H), 7.41 (s, 1H), 7.49 (s, 1H), 7.78 (d, 1H), 9.59 (s, 1H), 10.20 (s, 1H); m/z 503 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-1342f6f8dd04407b9bba82a38ca0d3c2
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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