Hydrochloric Acid → (3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acid

HRID 2428205Notes

Reaction equation

HRID 2428205 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[Cl:29])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:6]1)=[O:4].[OH-].[Na+].Cl>CO>[C:33]([O:32][C:30]([N:7]1[CH2:8][CH2:9][C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[Cl:29])=[CH:13][CH:12]=2)[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67148356(3R,4S)-4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

Product 1

HCID 59234216(3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound D7 (4.31 g, 8 mmol) in MeOH (50 mL) and aq. 1M NaOH (79 mL) was stirred at 80° C. for 8 h. The mixture was allowed to cool to rt, and aq. 2M HCl (50 mL) was added. The mixture was extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (4.18 g, quantitative yield). LC-MS: tR=1.12 min, ES+: 524.41.

Workup

  1. temperatureto cool to rt
  2. extractionThe mixture was extracted with EtOAc
  3. washextracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-a087b9ab4d724c8288334512c3b3e7ff
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…