Hydrochloric Acid → HCID 58537907, compound

HRID 1473760Notes

Reaction equation

HRID 1473760 reaction equation
C[O:2][C:3]([C:5]1([N:13]([CH3:26])[C:14](=[O:25])[CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)=O.C[O-].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[OH:2][C:3]1[C:5]2([CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]2)[N:13]([CH3:26])[C:14](=[O:25])[C:15]=1[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 58537950HCID 58537950, compound

Product 1

HCID 58537907HCID 58537907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methoxy-4-{methyl-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester (85.0 g, 234.5 mmol) in dimethylformamide (800 ml) at 0° C. was added sodium methoxide (38.0 g, 703.5 mmol) in four portions and stirring continued at 0° C. for 30 minutes, then at room temperature for 1 hour. The reaction mixture was poured on ice and saturated aqueous ammonium chloride, acidified to pH 5-6 with concentrated HCl and thoroughly extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, concentrated and the residue dried in vacuo. Yield: 72.7 g of 4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2.2) as a solid.

Workup

  1. waitat room temperature for 1 hour
  2. extractionthoroughly extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-c3e2f2519e8f4aaf87b24109840d1b56
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

Loading…