Tributylphosphine → HCID 57197175, compound

HRID 1167453Notes

Reaction equation

HRID 1167453 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1.O[C:30]1[CH:34]=[CH:33][O:32][N:31]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:17]([O:16][C:14]([NH:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:7]2[CH:6]=[CH:5][C:4]([N:21]3[CH2:25][C@H:24]([CH2:26][O:27][C:30]4[CH:34]=[CH:33][O:32][N:31]=4)[O:23][C:22]3=[O:28])=[CH:3][C:2]=2[F:1])[CH2:9]1)=[O:15])([CH3:18])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21356558HCID 21356558, compoundHCID 178516613HCID 178516613, compound

Product 1

HCID 57197175HCID 57197175, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Fluoro-4-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (5 g, 12.7 mmol), 3-hydroxyisoxazole (2.15 g, 25.3 mmol), and 1,1′-(azodicarbonyl)dipiperidine (6.39 g, 25.3 mmol) were suspended by stirring in dry tetrahydrofuran (100 ml) under nitrogen and cooled to 5° in an ice-bath. Tributylphosphine (5.12 g, 25.3 mmol) was added dropwise over 20 minutes, and the solution stirred 18 hours, allowing the temperature to rise to ambient. Reduced azo compound was filtered off, and the solution evaporated to dryness and the residue triturated with ether. The residue was purified by chromatography on a 90 g Biotage silica column, eluting with a gradient from 50 to 75% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the product (3.92 g).

Workup

  1. temperaturecooled to 5° in an ice-bath
  2. filtrationReduced azo compound was filtered off
  3. customthe solution evaporated to dryness
  4. customthe residue triturated with ether
  5. customThe residue was purified by chromatography on a 90 g Biotage silica column
  6. washeluting with a gradient from 50 to 75% EtOAc in isohexane
  7. customevaporated

Sources & evidence

ORD record
ord-3054dea443734790bed818f1ccab34ef
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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