Dimethylamine, hydrochloride → Tert-butyl(3r)-6-cyclohexyl-3-(3-{[[2-(dimethylamino)-2-oxoethyl](methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

HRID 1350251Notes

Reaction equation

[C:1]([O:5][C:6](=[O:30])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([CH2:23][N:24]([CH2:26][C:27](O)=[O:28])[CH3:25])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[NH:31]([CH3:33])[CH3:32].Cl>>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([CH2:23][N:24]([CH2:26][C:27]([N:31]([CH3:33])[CH3:32])=[O:28])[CH3:25])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:30])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 10473Dimethylamine, hydrochloride

HCID 60077601[({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid

Product 1

HCID 60077618Tert-butyl(3r)-6-cyclohexyl-3-(3-{[[2-(dimethylamino)-2-oxoethyl](methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Procedure

Method as for preparation 56 using [({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid (preparation 133) (725 mg, 1.71 mmol) and Me2NH.HCl (106 mg, 1.30 mmol) as starting materials.

Sources & evidence

ORD record: ord-124546b0c4864c76ab7905f892436ed6
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214694B2

Reaction notes

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