Acetic Acid → HCID 67670838, compound

HRID 1417556Notes

Reaction equation

HRID 1417556 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:30][CH2:29][C@:7]2([O:11][CH2:10][C:9]([C:12]3[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:26])([F:25])[F:24])[CH:15]=[CH:14][C:13]=3[O:27][CH3:28])=[CH:8]2)[C@@H:6]1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:4].C(O)(=O)C>[OH-].[Pd+2].[OH-].CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:30][CH2:29][C@:7]2([O:11][CH:10]=[C:9]([C:12]3[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:24])([F:25])[F:26])[CH:15]=[CH:14][C:13]=3[O:27][CH3:28])[CH2:8]2)[C@@H:6]1[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)=[O:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57147802HCID 57147802, compound

Product 1

HCID 67670838HCID 67670838, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 67 mg (0.13 mmol) of (5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-3-ene-7-carboxylic acid methyl ester (from Example 69), 20% palladium(II) hydroxide on carbon (32 mg), acetic acid (1.2 mL), and methanol (6.0 mL) was stirred at RT under hydrogen at atmospheric pressure. After 20 min., the catalyst was removed using a 0.45 micron filter and washed with additional methanol. The filtrate was concentrated and the residue was purified by preparative TLC, eluting five times in 3% ethyl ether in dichloromethane. This yielded 15 mg of the title compound and 30 mg of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester.

Workup

  1. customthe catalyst was removed
  2. filtrationfilter
  3. washwashed with additional methanol
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative TLC
  6. washeluting five times in 3% ethyl ether in dichloromethane

Sources & evidence

ORD record
ord-086cab47e4e34505b4156b0e33148b69
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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