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

HRID 1474694Notes

Reaction equation

HRID 1474694 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH:5]=[CH:4][C:3]=1[CH2:28][C:29]([O:31]C)=[O:30].[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[N:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][N:25]=3)[CH2:18][CH2:19]2)[CH:5]=[CH:4][C:3]=1[CH2:28][C:29]([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89583879Methyl [2-fluoro-4-(2-{(1S,2R)-2-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetate

Product 1

HCID 89583872[2-fluoro-4-(2-{(1S,2R)-2-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl [2-fluoro-4-(2-{(1S,2R)-2-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)phenyl]acetate (1.41 g, 3.28 mmol) was dissolved in MeOH (15 ml) and sodium hydroxide (5 M, 3.18 ml, 15.9 mmol) was added. The mixture was stirred at RT for 1 h and neutralized to pH 5 with 5 M HCl (5 ml), extracted with EtOAc (50 ml). The organic phase was dried over MgSO4, and evaporated to afford the title compound. LC/MS (m/z): 430 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-45e162ad916c435794fee46d80a8330e
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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