Hydrochloric Acid → [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetic acid

HRID 1474662Notes

Reaction equation

HRID 1474662 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29]C)=[O:28])=[CH:22][CH:21]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.CO.[OH-].[Li+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:24][CH:25]=3)[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 89583877Methyl [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetate

Product 1

HCID 89582225[4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetate (20 mg, 0.047 mmol) in 3 ml THF was added 1 ml methanol and 1 ml water. Lithium hydroxide (5.6 mg, 0.23 mmol) was added to the mixture, and the mixture was stirred at RT overnight. 1 M hydrochloric acid was added to adjust the pH to 4. The volatiles were removed under vacuum, and the remaining aqueous layer was extracted with dichloromethane (3×10 ml). The organics were combined, dried over magnesium sulphate, filtered, and the filtrate concentrated under reduced pressure to afford the title compound. LC/MS (m/z) 416.3 (M+H)+.

Workup

  1. customThe volatiles were removed under vacuum
  2. extractionthe remaining aqueous layer was extracted with dichloromethane (3×10 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b7c47b45d4f6480dbecdb373c54416e6
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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