2-Methoxyethylamine → HCID 54098238, compound

HRID 1108773Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl.[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:14]([OH:36])[CH2:15][NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH:19]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31](OCC)=[O:32])=[CH:25][CH:24]=3)[CH2:18]2)[CH:11]=[CH:12][CH:13]=1>>[Cl:7][C:8]1[CH:9]=[C:10]([C@@H:14]([OH:36])[CH2:15][NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH:19]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:32])=[CH:25][CH:24]=3)[CH2:18]2)[CH:11]=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 69972501HCID 69972501, compound

Product 1

HCID 54098238HCID 54098238, compoundYield 98.6%

Procedure

2-Methoxyethylamine (320 mg) was added to the (1R)-1-(3-chlorophenyl)-2-[3-(4-ethoxycarbonylmethoxyphenyl) cyclohexylamino]ethanol hydrochloride (trans-H) obtained in Example 28 (100 mg), and the mixture was stirred at room temperature for 71 hours. The reaction solution was separated and purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 97 mg of (2R)-2-[4-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy]-N-(2-methoxyethyl) acetamide (90% yield).

Workup

customThe reaction solution was separated
custompurified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-2f7c4d3bb3594d6898678f6893e5132a
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069176

Reaction notes

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