Hydrochloric Acid → HCID 178441229, compound

HRID 406281Notes

Reaction equation

HRID 406281 reaction equation
CC([N:5]([C@H:9]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:19]=[C:18]([F:20])[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])=[C:16]([F:25])[CH:15]=2)[CH2:10]1)C(=O)[O-])(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[CH3:24][C:21]([C:17]1[C:16]([F:25])=[CH:15][C:14]([O:13][C@@H:11]2[CH2:10][C@H:9]([NH2:5])[CH2:12]2)=[CH:19][C:18]=1[F:20])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178441232HCID 178441232, compound

Product 1

HCID 178441229HCID 178441229, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 1,1-dimethylethyl(cis-3-{[4-(1,1-dimethylethyl)-3,5-difluorophenyl]oxy}cyclobutyl)carbamate (6.85 g, 19.27 mmol) in 1,4-dioxane (50 mL) was added a solution of hydrogen chloride in 1,4-dioxane (50 mL, 4M, 200 mmol) in one charge. The reaction vessel was sealed and the reaction stirred at ambient temperature for 16 hours. The reaction was concentrated to approximately half volume in vacuo and the resultant slurry was diluted with diethyl ether (200 mL) and the mixture stirred rapidly for 10 min. The precipitate was collected by filtration and dried in vacuo to give the title compound as a white solid (3.39 g). The mother liquors were concentrated in vacuo to give a yellow sticky solid. Trituration with diethyl ether (ca 20 mL) gave a white precipitate, the precipitate was collected by filtration and dried in vacuo to give a further batch of the title compound (1.035 g).

Workup

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. concentrationThe reaction was concentrated to approximately half volume in vacuo
  4. additionthe resultant slurry was diluted with diethyl ether (200 mL)
  5. stirringthe mixture stirred rapidly for 10 min
  6. filtrationThe precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ca05047150f34cbabfa39b630f1e541c
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

Loading…