Ethanol → (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-5-ethoxy-2-fluoro-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester

HRID 1266714Notes

Reaction equation

HRID 1266714 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH:5]([C:15]1[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[F:40])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH3:2].[CH3:42][CH2:43]O.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:41])[CH:5]([C:15]1[CH:20]=[C:19]([O:21][CH2:42][CH3:43])[CH:18]=[C:17]([O:22][Si:23]([C:36]([CH3:37])([CH3:39])[CH3:38])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[F:40])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 97268Di-tert-butyl azodicarboxylateHCID 70004048(RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-5-hydroxy-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester

Product 1

HCID 70002436(RS)-[3-(tert-butyl-diphenyl-silanyloxy)-5-ethoxy-2-fluoro-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 49 g (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-5-hydroxy-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester described in example 3.3 in 900 ml THF 24.86 g triphenylphosphine, 5.53 ml EtOH and 21.82 g di-tert-butyl azodicarboxylate were added sequentially. The solution was stirred for 4 hrs at room temperature and then evaporated. The crude product was purified by chromatography on silica gel (cyclohexane/EtOAc) to yield 27.6 g (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-5-ethoxy-2-fluoro-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester as slightly yellow, amorphous solid.

Workup

  1. customevaporated
  2. customThe crude product was purified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-9713f5f1058c40ad8a60250bb6c8278d
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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