HCID 19753883, compound → 124073-08-1

HRID 1588816Notes

Reaction equation

HRID 1588816 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19753883HCID 19753883, compound

Product 1

HCID 19753820124073-08-1Yield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 5-(N-t-butoxycarbonyl-N-methylamino)valerate (557 mg) in methanol (6 ml) and 1N sodium hydroxide solution (3.41 ml) was stirred at ambient temperature for 1 hour. The solution was concentrated in vacuo, and the residue was poured into water (20 ml) and diethyl ether (20 ml). The aqueous layer was separated and acidified with 1N hydrochloric acid, and extracted with ethyl acetate (20 ml×3). The extract was collected and washed with water (40 ml×2) and brine (40 ml) successively, and dried over magnesium sulfate. Evaporation of the solvent gave 5-(N-t-butoxycarbonyl-N-methylamino)valeric acid (470 mg) as an oil.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue was poured into water (20 ml) and diethyl ether (20 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (20 ml×3)
  5. customThe extract was collected
  6. washwashed with water (40 ml×2) and brine (40 ml) successively
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-33f136306ca94bcf913490dcddb22571
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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