Trifluoroacetic acid → HCID 86698466, compound

HRID 527681Notes

Reaction equation

HRID 527681 reaction equation
CC([N:5]([C@:9]([C:13]([NH:15][C:16]1[CH:17]=[N:18][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]3[O:29][CH2:30][CH2:31][C:32]4([CH2:34][CH2:33]4)[C:24]=23)=[N:20][CH:21]=1)=[O:14])([CH3:12])[CH2:10][CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:32]12([C:24]3[C:25](=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:19]3[N:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C@:9]([CH3:12])([CH2:10][CH3:11])[NH2:5])=[CH:17][N:18]=3)[O:29][CH2:30][CH2:31]1)[CH2:33][CH2:34]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698467HCID 86698467, compound2×

Product 1

HCID 86698466HCID 86698466, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[(1R)-1-({[2-(2,3-dihydrospiro[chromene-4,1′-cyclopropan]-5-yloxy)-5-pyrimidinyl]amino}carbonyl)-1-methylpropyl]carbamate (Intermediate 224, 5 mg, 10.67 μmol) in dry Dichloromethane (1 mL) cooled to 0° C. TFA (0.822 μL, 10.67 μmol) was added dropwise. The reaction mixture was stirred for 2 hours at the same temperature. The reaction was allowed to reach room temperature then the volatiles were evaporated. The residue was diluted with DCM (2 mL), and washed with NaHCO3 sat. sol. (7 mL). The organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound (4 mg) as a yellow oil that was used in the next step without further purification.

Workup

  1. customto reach room temperature
  2. customthe volatiles were evaporated
  3. additionThe residue was diluted with DCM (2 mL)
  4. washwashed with NaHCO3 sat. sol. (7 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8727af0416e34a09870bd6e7198006e2
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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