4-Methylmorpholine → N-(2,4-dihydroxybutyl)-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzamide

HRID 558415Notes

Reaction equation

[OH:1][CH:2]([CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)[CH:11]=1)[CH2:3][C:4](O)=[O:5].CN1CCOCC1.ClC(OCC)=O.B.[Li]>O1CCCC1.O>[OH:1][CH:2]([CH2:3][CH2:4][OH:5])[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:22][CH:21]=2)[CH:11]=1

Participants

Conditions

Temperature: -15 °C

Procedure

The obtained 3-hydroxy-4-{4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoylamino}butyric acid (27 mg) and 15 μL of N-methylmorpholine were dissolved in 3 mL of tetrahydrofuran under an atmosphere of nitrogen, and the solution was cooled to −15° C. Ethyl chloroformate (13 μL) was added to the solution, the mixture was stirred for 15 minutes, and then 18.4 mg of lithium boron hydride was added. After the mixture was stirred for 30 minutes at −15° C., 1 mL of water was added, and the reaction was quenched. The reaction mixture was purified by preparative high-performance liquid chromatography to obtain 21 mg (78%) of N-(2,4-dihydroxybutyl)-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzamide.

Workup

stirringAfter the mixture was stirred for 30 minutes at −15° C.
customthe reaction was quenched
customThe reaction mixture was purified by preparative high-performance liquid chromatography

Sources & evidence

ORD record: ord-3ef304e03f1346e89d6528f2a83c09b0
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063046B2

Reaction notes

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