1-O-[(Z)-(1-amino-2-pyridin-4-ylethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate → tert-butyl (3R)-6-cyclohexyl-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoate

HRID 1279888Notes

Reaction equation

HRID 1279888 reaction equation
[NH2:1]/[C:2](=[N:10]\[O:11][C:12]([C@H:14]([CH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O)/[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1>C1(C)C(C)=CC=CC=1>[CH:26]1([CH2:25][CH2:24][CH2:23][C@@H:14]([C:12]2[O:11][N:10]=[C:2]([CH2:3][C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)[N:1]=2)[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

3

Reactant 1

HCID 167490061-O-[(Z)-(1-amino-2-pyridin-4-ylethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate

Product 1

HCID 16749537tert-butyl (3R)-6-cyclohexyl-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoateYield 63.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of tert-butyl (3R)-3-[({[(Z)-1-amino-2-(4-pyridinyl)ethylidene]amino}oxy)carbonyl]-6-cyclohexylhexanoate (Preparation 104) (840 mg, 1.60 mmol) in xylene (15 ml) was heated at 130° C. for 4.5 hours. After cooling to room temperature the reaction mixture was purified by column chromatography on silica gel eluting with a gradient system of 90:10 (pentane:ethyl acetate) gradually changing to 50:50 (pentane:ethyl acetate) to afford the title compound as a yellow oil (420 mg).

Workup

  1. customwas purified by column chromatography on silica gel eluting with a gradient system of 90:10 (pentane:ethyl acetate)

Sources & evidence

ORD record
ord-20849a6631ac4bf5a7fb5887ea1597b5
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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