Hydrochloric Acid → cis(+/-)-3-(4-{[(Benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoic acid

HRID 1424954Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl cis(±)-3-(4-{[benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate obtained in Example (42a) (250 mg, 0.63 mmol) was dissolved in methanol (5 mL). A 1 N aqueous sodium hydroxide solution (4 mL) was added, and the mixture was stirred at 70° C. for one hour. The reaction solution was neutralized with 1 N hydrochloric acid, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

extractionfollowed by extraction with ethyl acetate
washThen, the organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record: ord-d9fa58e927984c75a689d1369780e011
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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