Hydrochloric Acid → 2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetic acid

HRID 1850777Notes

Reaction equation

HRID 1850777 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30]C)=[O:29])=[CH:23][CH:22]=3)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[OH-].[Li+].Cl>CO.O>[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][C:28]([OH:30])=[O:29])=[CH:25][CH:26]=3)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70856387Methyl 2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetate

Product 1

HCID 708186952-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetic acidYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetate (0.55 g, 1.28 mmol) was dissolved in MeOH (5 ml) and lithium hydroxide (154 mg, 6.43 mmol) in 2 mL of water was added. The mixture was stirred at RT for 1 h and neutralized to pH 6 with 5 N HCl, extracted with EtOAc (50 ml). The EtOAc phase was dried over MgSO4, and evaporated to afford 514 mg (97%) of the desired product. LC/MS (m/z): 414 (M+H)+.

Workup

  1. extractionextracted with EtOAc (50 ml)
  2. dry with materialThe EtOAc phase was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-9a6bf43ddfda45639ef4309642fa3496
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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