Sodium Hydroxide → HCID 131710448, compound

HRID 1576070Notes

Reaction equation

HRID 1576070 reaction equation
C([NH:4][C:5]1[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[S:7][CH2:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[S:7][CH2:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54233282HCID 54233282, compound

Product 1

HCID 131710448HCID 131710448, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of 8.2 g (.022 mole) of 3-acetamido-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid piperidide in 80 ml of methanol was added 40 ml of 1 N sodium hydroxide. The reaction was stirred at room temperature (22°C.) for 3 hrs. and was immediately worked up by first removing methanol under vacuum. The aqueous, basic residue was partitioned between 50 ml of water and 100 ml of methylene chloride. The basic, aqueous phase was extracted three times with 30 ml portions of methylene chloride. The methylene chloride was dried over sodium sulfate, filtered, and evaporated to afford 2.45 g (0.0075 mole, 34%) of 3-amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid piperidide.

Workup

  1. customThe aqueous, basic residue was partitioned between 50 ml of water and 100 ml of methylene chloride
  2. extractionThe basic, aqueous phase was extracted three times with 30 ml portions of methylene chloride
  3. dry with materialThe methylene chloride was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c7eaceb64d83471ead12d744d661af94
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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