Hydrochloric Acid → HCID 58280270, compound

HRID 2189080Notes

Reaction equation

HRID 2189080 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][CH2:5][C@@H:6]1[CH2:11][C@H:10]([O:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[C:20]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:9][CH2:8][N:7]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[OH-].[Na+].Cl>CO>[C:39]([O:38][C:36]([N:7]1[CH2:8][CH2:9][C@@H:10]([O:12][C:13]2[C:14]3[C:21]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)=[C:20]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:11][C@H:6]1[CH2:5][CH2:4][C:3]([OH:43])=[O:2])=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58280123HCID 58280123, compound

Product 1

HCID 58280270HCID 58280270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 35 mg (0.06 mmol) of 3-[(2R,4R)-1-(tert-butoxycarbonyl)-4-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}piperidin-2-yl]propanoic acid methyl ester in 0.1 ml of methanol, cool to 0° C. and add approx. 240 mg of 10% sodium hydroxide solution. Stir the mixture at approx. 40° C. for several hours, then at RT overnight. Then slightly acidify the reaction mixture with 1N hydrochloric acid (pH approx. 3) and extract repeatedly with dichloromethane. Wash the combined organic phases with satd. sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. The target compound is obtained in quantitative yield (34 mg) and is not purified further.

Workup

  1. customat RT
  2. customovernight
  3. extractionextract repeatedly with dichloromethane
  4. washWash the combined organic phases with satd
  5. dry with materialsodium chloride solution, dry over magnesium sulphate
  6. concentrationconcentrate under reduced pressure
  7. customThe target compound is obtained in quantitative yield (34 mg)
  8. customis not purified further

Sources & evidence

ORD record
ord-d62b963d7e544cb790caf2206189faa8
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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