Hydrochloric Acid → HCID 86717804, compound

HRID 1468874Notes

Reaction equation

HRID 1468874 reaction equation
Cl.O1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]([CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[CH:12]=[CH:13][C:14]=1[CH2:15][O:16][CH2:17][C@@H:18]1[CH2:20][C@@H:19]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[O:31][N:30]=[C:29]([CH:32]([CH3:34])[CH3:33])[N:28]=2)[CH2:23][CH2:22]1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH2:35][C:36]([OH:38])=[O:37])[CH:12]=[CH:13][C:14]=1[CH2:15][O:16][CH2:17][C@@H:18]1[CH2:20][C@@H:19]1[CH:21]1[CH2:22][CH2:23][N:24]([C:27]2[O:31][N:30]=[C:29]([CH:32]([CH3:34])[CH3:33])[N:28]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71136852tert-butyl 2-(3-fluoro-4-((((1R,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)methoxy)methyl)phenyl)acetate

Product 1

HCID 86717804HCID 86717804, compoundYield 158%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 4 M HCl in dioxane (3.85 mL, 15.4 mmol) was added to a solution of tert-butyl 2-(3-fluoro-4-((((1R,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)methoxy)methyl)phenyl)acetate (Step C product, 750 mg, 1.54 mmol) in DCM (4 mL). This mixture was stirred at 35° C. for 4 hrs. The reaction mixture was subsequently concentrated under reduced pressure to afford the title compound (1.05 g, 97%) as a crude product to be used for the next step. LC/MS (m/z): 432 (M+H)+.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated under reduced pressure

Sources & evidence

ORD record
ord-909905d49c944a208846da1323de0015
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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