Aldoxime → 3-[3-(3-Methyl-isoxazol-5-yl)-phenyl)-3-oxo-propionic acid tert-butyl ester

HRID 1062009

Reaction equation

HRID 1062009 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12]CC)=O)[O:4][N:3]=1.C(C1C=C(C=CC=1)C(OCC)=O)#C.C1C(=O)N(Cl)C(=O)C1.C(=NO)C.[C:43]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])(=[O:45])[CH3:44].[Li]>C(Cl)(Cl)Cl.N1C=CC=CC=1.CCN(CC)CC>[C:47]([O:46][C:43](=[O:45])[CH2:44][C:10]([C:9]1[CH:15]=[CH:16][CH:17]=[C:7]([C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)[CH:8]=1)=[O:12])([CH3:50])([CH3:49])[CH3:48]

Participants

9

Reactant 5

HCID 7863AldoximeHCID 31398ChlorosuccinimideHCID 15540684Ethyl 3-ethynylbenzoateHCID 22224947Ethyl 3-(3-methyl-isoxazol-5-yl)-benzoateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 695928713-[3-(3-Methyl-isoxazol-5-yl)-phenyl)-3-oxo-propionic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Prepared from ethyl 3-(3-methyl-isoxazol-5-yl)-benzoate [prepared by reaction of ethyl 3-ethynylbenzoate [CAS-No. 178742-95-5] with a mixture of NCS, acetaldoxime, Et3N and cat. amount of pyridine in CHCl3 at 50° C. according to Tetrahedron 1984, 40, 2985-2988] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as a yellow solid (2.54 g).

Workup

  1. customat 50° C.

Sources & evidence

ORD record
ord-ffd75cd159094159ae215646f909a3c5
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Linked notes

Loading…