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

HRID 8149
Notes
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Reaction equation

HRID 8149 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25](C)[C@H:24](O)[O:23][C:22]3=[O:28])=[CH:17][C:16]=2[F:29])[CH:14]=1)(C(C)(C)C)(C)C.C(O[C:35]([NH:37][C:38]1[CH:42]=[CH:41][O:40][N:39]=1)=O)(C)(C)C.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[O:40]1[CH:41]=[CH:42][C:38]([NH:37][CH2:35][C@@H:24]2[O:23][C:22](=[O:28])[N:21]([C:18]3[CH:19]=[CH:20][C:15]([N:13]4[CH:14]=[C:10]([CH2:9][OH:8])[N:11]=[CH:12]4)=[C:16]([F:29])[CH:17]=3)[CH2:25]2)=[N:39]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamateHCID 695835493-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-hydroxy-methyloxazolidin-2-one

Product 1

HCID 497419(5S)-3-[3-fluoro-4-[4-(hydroxymethyl)imidazol-1-yl]phenyl]-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one
Yield 13.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-hydroxy-methyloxazolidin-2-one (842 mg, 2 mM, see WO 97-31917) and 3-(t-butoxycarbonyl-amino)isoxazole (405 mg, 2.2 mM) were suspended by stirring in dry tetrahydrofuran (15 ml) under nitrogen in an ice-bath. Tributylphosphine (444 mg, 2.2 mM) followed by 1,1′-(azo-dicarbonyl)dipiperidine (555 mg, 2.2 mM) dissolved in tetrahydrofuran (10 ml) were added. 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 10 g reversed phase C18 column, eluting with a gradient from 10 to 50% acetonitrile in water containing 0.1% trifluoroacetic acid. Relevant fractions were combined, evaporated, and the residue rechromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 20% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (104 mg). MS (ESP): 474 (MH+) for C22H24FN5O6

Workup

  1. additionwere added
  2. filtrationthen filtered
  3. washthe filter cake washed with tetrahydrofuran
  4. customThe combined filtrates were evaporated
  5. customthe residue purified by chromatography on a 10 g
  6. washeluting with a gradient from 10 to 50% acetonitrile in water containing 0.1% trifluoroacetic acid
  7. customevaporated
  8. customthe residue rechromatographed on a 10 g silica Mega Bond Elut® column
  9. washeluting with
  10. temperaturea gradient increasing in polarity from 0 to 20% methanol in dichloromethane
  11. customevaporated

Sources & evidence

ORD record
ord-f117782d22684c3b8f592482d3de22f8
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087629B2

Reaction notes

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