Hydrochloric Acid → HCID 86759435, compound

HRID 2088200Notes

Reaction equation

HRID 2088200 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([N:16]3[CH:20]=[N:19][N:18]=[N:17]3)[CH2:15][C@@:9]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:10]([O:21][C@H:22]([C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH3:23])[CH2:11][CH2:12]2)C1C=CC=CC=1.[ClH:44]>CO.C(OCC)C.[OH-].[Pd+2].[OH-]>[ClH:44].[F:32][C:30]([F:31])([F:33])[C:28]1[CH:29]=[C:24]([C@@H:22]([O:21][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:15][C@H:14]3[N:16]2[CH:20]=[N:19][N:18]=[N:17]2)[CH3:23])[CH:25]=[C:26]([C:34]([F:35])([F:37])[F:36])[CH:27]=1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86759433HCID 86759433, compound

Product 1

HCID 86759435HCID 86759435, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-1-phenyl-6-(1H-tetrazol-1-yl)-8-azabicyclo[3.2.1]octane (Example 135; 158 mg, 0.26 mmol) was dissolved in methanol (5 ml) and 2N hydrochloric acid (0.5 ml) and 10% palladium hydroxide (40 mg) added and the mixture hydrogenated at 50 psi for 30 minutes. The reaction mixture was then filtered and concentrated in vacuo. The oil was partitioned between saturated sodium hydrogen carbonate solution and dichloromethane and the organics dried (MgSO4) and concentrated in vacuo to give a yellow oil. This was purified by thin layer chromatography [5% methanol in dichloromethane] to give a white solid. The hydrochloride salt was made by adding 1 equivalent of hydrogen chloride in diethyl ether to a solution in diethyl ether and the title compound filtered and dried in vacuo at 60° C. (41 mg, 28%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe oil was partitioned between saturated sodium hydrogen carbonate solution and dichloromethane
  4. dry with materialthe organics dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThis was purified by thin layer chromatography [5% methanol in dichloromethane]
  8. customto give a white solid
  9. filtrationthe title compound filtered
  10. customdried in vacuo at 60° C. (41 mg, 28%)

Sources & evidence

ORD record
ord-2a5093353cbf4a11b779b9c93fc55146
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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