Hydrochloric Acid → Hydrochloric Acid

HRID 1506355Notes

Reaction equation

[OH:1][CH:2]([C:16]1[CH:17]=[C:18]2[C:41](=[CH:42][CH:43]=1)[C:22]1=[N:23][O:24][C:25]([C:26]3[C:30]([C:31]([F:34])([F:33])[F:32])=[C:29]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[O:28][N:27]=3)=[C:21]1[CH2:20][CH2:19]2)[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([CH2:10][C:11]([O:13]CC)=[O:12])[CH2:5]1.C(#N)C.[ClH:47]>O>[OH:1][CH:2]([C:16]1[CH:17]=[C:18]2[C:41](=[CH:42][CH:43]=1)[C:22]1=[N:23][O:24][C:25]([C:26]3[C:30]([C:31]([F:34])([F:33])[F:32])=[C:29]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[O:28][N:27]=3)=[C:21]1[CH2:20][CH2:19]2)[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([CH2:10][C:11]([OH:13])=[O:12])[CH2:5]1.[ClH:47]

Participants

Conditions

Temperature: 60 °C

Procedure

To ethyl 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetate (Preparation 19A, 125 mg, 0.210 mmol were added acetonitrile (3 mL) and 6N hydrochloric acid (3 mL). The reaction mixture was heated at 60° C. for 4 h. The reaction mixture was concentrated under reduced pressure to yield a solid. To the solid was added acetonitrile (0.5 mL) and water (10 mL). The contents were sonicated and lyophilized to yield 2-((3R)-1-(2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)piperidin-3-yl)acetic acid, hydrochloric acid (150 mg, 0.248 mmol, 70.3% yield) as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto yield a solid
customThe contents were sonicated

Sources & evidence

ORD record: ord-cb69998140624ab2a0ab5d35710f5ac5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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