Sodium Hydroxide → HCID 25096159, compound

HRID 1926935Notes

Reaction equation

HRID 1926935 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][CH2:6][N:7]([CH2:9][CH:10]([O:12][C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[C:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1)[CH3:11])[CH3:8].[OH-].[Na+]>C1COCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([O:12][CH:10]([CH3:11])[CH2:9][N:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58016774HCID 58016774, compound

Product 1

HCID 25096159HCID 25096159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Put 20 mg (0.027 mmol) (+/−)-4-[(2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propyl)(methyl)amino]butanoic acid methyl ester in 0.8 ml THF. Add 0.27 ml (0.27 mmol) 1 N sodium hydroxide solution and stir overnight at RT. Then concentrate by evaporation and purify the residue by thick-layer chromatography on silica gel (solvent: dichloromethane/methanol 9:1). Extract the product zone with dichloromethane/methanol 7:3. 8.5 mg (66.3% of theor.) of the target compound is obtained.

Workup

  1. concentrationThen concentrate by evaporation
  2. custompurify the residue by thick-layer chromatography on silica gel (solvent: dichloromethane/methanol 9:1)
  3. extractionExtract the product zone with dichloromethane/methanol 7:3
  4. custom8.5 mg (66.3% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-a39c86b9b88943d795e29ef31f776716
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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