Hydrochloric Acid → HCID 58016928, compound

HRID 1926922Notes

Reaction equation

HRID 1926922 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[OH-].[Na+].Cl>CO.C1COCC1.O>[C:19]1([C:18]2[C:11]3[C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])=[N:15][CH:14]=[N:13][C:12]=3[O:16][C:17]=2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58016808HCID 58016808, compound

Product 1

HCID 58016928HCID 58016928, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 27.5 mg (0.066 mmol) 6-[(5,6-diphenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoic acid methyl ester in 0.1 ml methanol, 0.05 ml THF and one drop of water and add 0.09 ml 2.5 M sodium hydroxide solution. Stir the mixture for 1 h at RT and then lightly acidify with 1 N hydrochloric acid. Extract the aqueous phase three times with dichloromethane. Combine the organic phases and dry over magnesium sulphate, concentrate by vacuum evaporation and dry the residue at high vacuum. 25 mg (96.1% of theor.) of the target compound is obtained.

Workup

  1. extractionExtract the aqueous phase three times with dichloromethane
  2. dry with materialdry over magnesium sulphate
  3. concentrationconcentrate by vacuum evaporation
  4. customdry the residue at high vacuum
  5. custom25 mg (96.1% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-1805aafd4a3f4c01a1b1aeeb61f70827
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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