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Tributylphosphine → (5S)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one

HRID 8147
Notes
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Reaction equation

HRID 8147 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][C@H:15]([CH2:17]O)[O:14][C:13]3=[O:19])=[CH:8][C:7]=2[F:20])[CH:5]=[CH:4][N:3]=[CH:2]1.ClC(Cl)(Cl)COC([NH:27][C:28]1[CH:32]=[CH:31][O:30][N:29]=1)=O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[O:30]1[CH:31]=[CH:32][C:28]([NH:27][CH2:17][C@@H:15]2[O:14][C:13](=[O:19])[N:12]([C:9]3[CH:10]=[CH:11][C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[C:7]([F:20])[CH:8]=3)[CH2:16]2)=[N:29]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 12114192,2,2-Trichloroethyl isoxazol-3-ylcarbamateHCID 104927643-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one

Product 1

HCID 497417(5S)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one
Yield 158.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(4-Imidazol-1-yl-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (693 mg, 2.5 mM, see WO 96-23788) and 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (649 mg, 2.5 mM) were suspended by stirring in dry tetrahydrofuran (25 ml) under nitrogen in an ice-bath. Tributylphosphine (808 mg, 4 mM) was added followed by 1,1′-(azodicarbonyl)dipiperidine (945 mg, 3.75 nM) dissolved in tetrahydrofuran (10 ml) over 10 minutes. The mixture was then stirred 18 hours, allowing the temperature to rise to ambient, then filtered, and the filter cake washed with tetrahydrofuran. The combined filtrates were evaporated and the residue purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined, evaporated, and the residue triturated with diethyl ether to give the desired product (1.36 g), contaminated with tributylphosphine oxide.

Workup

  1. filtrationthen filtered
  2. washthe filter cake washed with tetrahydrofuran
  3. customThe combined filtrates were evaporated
  4. customthe residue purified by chromatography on a 20 g silica Mega Bond Elut® column
  5. washeluting with
  6. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  7. customevaporated
  8. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-a99a9a93cf9f400f97f0c5d45b51636c
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087629B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes