Hydrochloric Acid → HCID 18770431, compound

HRID 479384Notes

Reaction equation

HRID 479384 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-5e6b0a1e4d98465e9d3f41b541ef13fd
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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