Hydrochloric Acid → HCID 18770431, compound

HRID 1279428Notes

Reaction equation

HRID 1279428 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH:17]([CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:18]([O:20]C)=[O:19])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>CO>[C:32]([O:31][C:29]([N:26]1[CH2:25][CH2:24][CH:23]([CH2:22][CH:17]([CH2:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:11][CH2:12]2)[C:18]([OH:20])=[O:19])[CH2:28][CH2:27]1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18770408HCID 18770408, compound

Product 1

HCID 18770431HCID 18770431, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous 5N sodium hydroxide (5 ml; 25 mmol) was added to a solution in methanol (5 ml) of methyl 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]acetate (906 mg; 1.9 mmol) synthesized by the process described in Referential Example 3, and the mixture was stirred for 30 minutes in a bath controlled at 100° C. The reaction mixture was made acidic by addition of 6N hydrochloric acid and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 861 mg (yield: 98%) of 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]acetic acid as a colorless oil.

Workup

  1. customsynthesized by the process
  2. customcontrolled at 100° C
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dbe238f7a3cb44b5ba8bec2d32225247
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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