Ethyl Acetate → (RS)-(4-cyano-phenylamino)-(5-ethoxy-2-fluoro-3-hydroxy-phenyl)-acetic acid ethyl ester

HRID 1266715Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:43])[CH:5]([C:15]1[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[CH:18]=[C:17]([O:24][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:16]=1[F:42])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:43])[CH:5]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)[C:15]1[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[CH:18]=[C:17]([OH:24])[C:16]=1[F:42])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 27.6 g (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-5-ethoxy-2-fluoro-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester described in example 3.4 in 470 ml THF was cooled to 0° C. and treated with 50.9 ml 1M tetrabutylammonium fluoride solution in THF. The reaction mixture was stirred at 0° C. for 4 hrs. The crude product was isolated by extraction with EtOAc and purified by chromatography on silica gel (cyclohexane/EtOAc) to yield 12.89 g (RS)-(4-cyano-phenylamino)-(5-ethoxy-2-fluoro-3-hydroxy-phenyl)-acetic acid ethyl ester as a yellow semisolid.

Workup

custompurified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record: ord-b8241d2b0a2e4c3f8ba7dfb7973fea39
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548694B2

Reaction notes

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