Methanol → HCID 2756027, compound

HRID 975781Notes

Reaction equation

HRID 975781 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:29][CH2:28][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:22][C:23]([O:25]C)=[O:24])[C:12]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][N:13]([CH2:22][C:23]([OH:25])=[O:24])[C:12]2=[O:27])[CH2:28][CH2:29]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 10692530HCID 10692530, compound

Product 1

HCID 2756027HCID 2756027, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2.96 g (7.8 mmol) of methyl 8-(t-butoxycarbonyl)-4-keto-1-phenyl-1.3.8-triazaspiro[4.5]decan-3-acetate, 2.03 g (14.7 mmol) of potassium carbonate, 30 ml of methanol and 10 ml of water was heated under reflux for 2 hours. The mixture was concentrated to about one-third of its original volume, diluted with 20 ml of water and acidified with 2N HCl at 0° C. The mixture was extracted with ethyl acetate and the extracts were washed with water and brine, dried, and concentrated in vacuo. Recrystallization of the residual solid from ethanol afforded 2.47 g (86%) of colorless crystals, mp 200°-201° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe mixture was concentrated to about one-third of its original volume
  4. additiondiluted with 20 ml of water
  5. customacidified with 2N HCl at 0° C
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe extracts were washed with water and brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customRecrystallization of the residual solid from ethanol

Sources & evidence

ORD record
ord-86615589b55c41c8bc4dd8cabcacee91
Source dataset
uspto-grants-1997_03
Patent number
US05610142

Reaction notes

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