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

HRID 646371Notes

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-d072eba98f994e41bff0c878e2944832
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705053B2

Reaction notes

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