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Boron trifluoride etherate → (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-5-hydroxy-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester

HRID 1266713
Notes
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Reaction equation

HRID 1266713 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([F:15])=[C:11]([CH:14]=1)C=O)(C)(C)C.[NH2:36][C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1.C1(C)C=CC(S(C[N+]#[C-])(=O)=[O:52])=CC=1.B(F)(F)F.[CH3:62][CH2:63][O:64][CH2:65][CH3:66]>CCO.CCOC(C)=O.O>[CH2:63]([O:64][C:65](=[O:52])[CH:66]([C:11]1[CH:14]=[C:7]([OH:6])[CH:8]=[C:9]([O:16][Si:17]([C:30]([CH3:32])([CH3:33])[CH3:31])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:10]=1[F:15])[NH:36][C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1)[CH3:62]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8000Boron trifluoride etherateHCID 133964-AminobenzonitrileHCID 161915Tosylmethyl isocyanideHCID 185518525-(Tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-benzaldehyde

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 35.0 g 5-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-benzaldehyde described in example 3.2 and 8.13 g 4-aminobenzonitrile in 250 ml EtOH was stirred for 1 hr at r.t. Then 13.43 g toluene-4-sulfonylmethyl isocyanide were added. The solution was cooled to 0° C. Subsequently, 25.9 ml of boron trifluoride diethyl etherate were added in a manner such that the temperature did not exceed 5° C. The mixture was stirred for 15 min at 0° C. and for 2 hrs at r.t. and subsequently treated with 25 ml H2O. The solution was stirred at 50° C. over night. The crude product was isolated by extraction with EtOAc and purified by chromatography on silica gel (cyclohexane/EtOAc) to yield 22.38 g (RS)-[3-(tert-butyl-diphenyl-silanyloxy)-2-fluoro-5-hydroxy-phenyl]-(4-cyano-phenylamino)-acetic acid ethyl ester as amorphous, slightly yellow solid.

Workup

  1. temperatureThe solution was cooled to 0° C
  2. customdid not exceed 5° C
  3. stirringThe mixture was stirred for 15 min at 0° C. and for 2 hrs at r.t.
  4. stirringThe solution was stirred at 50° C. over night
  5. custompurified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-9201f4784e2941e5acb6d4129ce5fb08
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06548694B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes