Hydrochloric Acid → HCID 57259682, compound

HRID 2289344Notes

Reaction equation

HRID 2289344 reaction equation
C[O:2][C:3]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:12][C:11]=2[O:30][CH3:31])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl.CCN(C(C)C)C(C)C.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>CO>[C:23]([N:20]1[CH2:21][CH2:22][CH:17]([O:16][C:13]2[CH:14]=[CH:15][C:10]([C:5]3([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]3)=[C:11]([O:30][CH3:31])[CH:12]=2)[CH2:18][CH2:19]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86755556HCID 86755556, compound

Product 1

HCID 57259682HCID 57259682, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(1-(1-(4-(N-Boc-4-piperidinyloxy)-2-methoxyphenyl)cyclopentylcarboxylic acid methyl ester (0.20 g, 0.46 mmol) from Step 7 above in MeOH (5 mL) was added aqueous NaOH (1.15 mL of a 2.0 N solution, 2.3 mmol). The mixture was refluxed for 5 days. The mixture was acidified to pH 2 by the addition of 2 N aqueous HCl and the solvent was removed under reduced pressure. The residue was suspended in DMF (5 mL) and to the mixture was added DIEA (0.17 mL, 1.0 mmol) and di-tert-butyldicarbonate (0.10 g, 0.46 mmol) were added and the mixture was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (50 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was washed with water (25 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 1-(1-(1-(4-(N-Boc-4-piperidinyloxy)-2-methoxyphenyl)cyclopentylcarboxylic acid as an amorphous solid (HPLC retention time=10.0 min (method A)).

Workup

  1. temperatureThe mixture was refluxed for 5 days
  2. customthe solvent was removed under reduced pressure
  3. additionwere added
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between EtOAc (50 mL) and 0.25 M aqueous citric acid (25 mL)
  6. washThe organic phase was washed with water (25 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4763428be39e4aaa83ce1ff5285e10c2
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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