Hydrochloric Acid → 2-(4-(2-((1S,2R)-2-(1-(5-ethoxypyrimidin-2-yl)piperidin-4-yl)cyclopropyl)ethoxy)-2,6-difluorophenyl)acetic acid

HRID 1474732Notes

Reaction equation

Cl.O1CCOCC1.[CH2:8]([O:10][C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([C@H:23]3[CH2:25][C@H:24]3[CH2:26][CH2:27][O:28][C:29]3[CH:34]=[C:33]([F:35])[C:32]([CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[C:31]([F:44])[CH:30]=3)[CH2:19][CH2:18]2)=[N:15][CH:16]=1)[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([C@H:23]3[CH2:25][C@H:24]3[CH2:26][CH2:27][O:28][C:29]3[CH:34]=[C:33]([F:35])[C:32]([CH2:36][C:37]([OH:39])=[O:38])=[C:31]([F:44])[CH:30]=3)[CH2:19][CH2:18]2)=[N:15][CH:16]=1)[CH3:9]

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of 4 M HCl in dioxane (16.2 mL, 64.7 mmol) was added to a solution of tert-butyl 2-(4-(2-((1S,2R)-2-(1-(5-ethoxypyrimidin-2-yl)piperidin-4-yl)cyclopropyl)ethoxy)-2,6-difluorophenyl)acetate (3.35 g, 6.47 mmol) in DCM (16 mL). This mixture was stirred at 35° C. for 4 hrs. The mixture was concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 462 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-9612efea62fa4052bbb60a7f67027215
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018224B2

Reaction notes

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