1-O-[(Z)-(1-amino-2-ethoxy-2-oxoethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate → ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

HRID 2084517Notes

Reaction equation

HRID 2084517 reaction equation
[NH2:1]/[C:2](=[N:8]\[O:9][C:10]([C@H:12]([CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=O)/[C:3]([O:5][CH2:6][CH3:7])=[O:4]>C1(C)C(C)=CC=CC=1>[C:17]([O:16][C:14](=[O:15])[CH2:13][C@H:12]([C:10]1[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:1]=1)[CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 1

HCID 591106871-O-[(Z)-(1-amino-2-ethoxy-2-oxoethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate

Product 1

HCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylateYield 99.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of tert-Butyl (3R)-3-[({[(Z)-1-amino-2-ethoxy-2-oxoethylidene]amino}oxy)carbonyl]-6-cyclohexylhexanoate (Preparation 169) (21.0 g, 50.82 mmol) in xylene (400 ml) was heated at 130° C. for 17 hours, then allowed to cool to room temperature. The residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (5:95) gradually changing to ethyl acetate:pentane (20:80) to afford the title compound as a colourless oil (20.0 g).

Workup

  1. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (5:95)

Sources & evidence

ORD record
ord-9f94b696ad144e229877f6e4a016e4f2
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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