Hydrochloric Acid → HCID 86730347, compound

HRID 1427046Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]2)=[CH:10][CH:9]=1)=[O:7])C.Cl>O1CCCC1.CO.C(OCC)(=O)C>[C:21]([O:20][C:18]([N:16]1[CH2:15][CH:14]([C:11]2[CH:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:13][CH:12]=2)[CH2:17]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 60 °C

Procedure

A 2 M sodium hydroxide solution (28.5 mL, 57.0 mmol) was added to a solution of tert-butyl 3-(4-(ethoxycarbonyl)phenyl)azetidine-1-carboxylate described in Production Example 26-4 (4.35 g, 14.2 mmol) in tetrahydrofuran (32 mL) and methanol (7 mL) at 25° C. The reaction liquid was stirred at 60° C. for 1 hour. 2 M hydrochloric acid (28.5 mL) was added to the reaction liquid, and the mixture was diluted with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to obtain the title compound (3.4 g, 86%).

Workup

customThe reaction liquid
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous sodium sulfate
customThe drying agent was separated by filtration
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1)

Sources & evidence

ORD record: ord-ddcaf09bed4e4ff08ad4ad13d7797b5d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

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