Ammonium Chloride → HCID 58428064, compound

HRID 1473782Notes

Reaction equation

HRID 1473782 reaction equation
C[O:2][C:3]([C:5]1([N:13]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[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+]>CN(C)C=O>[CH:27]1([O:26][N:13]2[C:5]3([CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]3)[C:3]([OH:2])=[C:15]([C:16]3[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=3[CH3:22])[C:14]2=[O:25])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 58428003HCID 58428003, compound

Product 1

HCID 58428064HCID 58428064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{cyclohexyloxy-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-1-methoxy-piperidine-4-carboxylic acid methyl ester (600 mg, 1.34 mmol) in dimethylformamide (10 ml) at 0° C. was added sodium methoxide (217 mg, 4.02 mmol) in one portion and the mixture was stirred at room temperature overnight. The reaction mixture was poured on cold saturated aqueous ammonium chloride and thoroughly extracted with ethyl acetate (4×25 ml). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:1). Yield: 329 mg of 1-cyclohexyloxy-4-hydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2ii.26) as a slight tan foam. Trituration with hexane gave a white solid, mp 115-118° C.

Workup

  1. extractionthoroughly extracted with ethyl acetate (4×25 ml)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:1)
  6. customTrituration with hexane gave a white solid, mp 115-118° C.

Sources & evidence

ORD record
ord-d86964f7915047138b6eb3f21f1dc747
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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