Trifluoroacetic acid → HCID 67966824, compound

HRID 527598Notes

Reaction equation

HRID 527598 reaction equation
CC([N:5]([C:9]([CH3:33])([CH3:32])[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][C:20]2[C:21]3[CH:22]4[CH2:30][C:23]4([CH3:31])[CH2:24][O:25][C:26]=3[CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:18]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:33][C:9]([C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][C:20]2[C:21]3[CH:22]4[CH2:30][C:23]4([CH3:31])[CH2:24][O:25][C:26]=3[CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:18]=1)=[O:11])([CH3:32])[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698436HCID 86698436, compound2×

Product 1

HCID 67966824HCID 67966824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[1,1-dimethyl-2-({6-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinyl}amino)-2-oxoethyl]carbamate (Intermediate 128, 135 mg, 0.298 mmol) in dry dichloromethane (10 ml) at 0° C. TFA (5 ml, 64.9 mmol) was slowly added and the reaction mixture was stirred for 2 hours at the same temperature. The solvent and the excess of TFA were evaporated and the residue was dissolved in dichloromethane and a saturated solution of NaHCO3 was slowly added while the pH was allowed to reach 8. Two phases were separated and the organic layer was dried over sodium sulphate, filtered and evaporated affording the title compound as a colourless oil used as it was without any further purification (105 mg).

Workup

  1. customat 0° C
  2. customThe solvent and the excess of TFA were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additiona saturated solution of NaHCO3 was slowly added while the pH
  5. customTwo phases were separated
  6. dry with materialthe organic layer was dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8c1dc0d4b8ad4c0887c3661be5f5395b
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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