Triphenylphosphine → HCID 86715104, compound

HRID 533913Notes

Reaction equation

HRID 533913 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=2)=[N:6][CH:7]=1.O[C@H:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(OCC)(=O)C.C1COCC1>[O:23]=[C:19]1[C@H:18]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[S:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=3)=[N:6][CH:7]=2)[CH2:22][CH2:21][NH:20]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11029774(3S)-3-hydroxypyrrolidin-2-oneHCID 136377298HCID 136377298, compound

Product 1

HCID 86715104HCID 86715104, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottomed flask was added methyl 2-(5-hydroxypyridin-2-yl)thiazole-5-carboxylate (400 mg), (S)-3-hydroxy-pyrrolidin-2-one (188 mg), PPh3 (443 mg), and THF (10 mL). DEAD (299 mg) was added dropwise at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours. After being diluted with ethyl acetate (50 mL), the organic layer was washed with water (20 mL×2) and brine (10 mL) and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the residue obtained was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1 to 1:3) to afford the subtitle compound. MS ESI+: m/z=320 [M-FH]+.

Workup

  1. washthe organic layer was washed with water (20 mL×2) and brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationAfter filtration and evaporation of the solvent
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography
  6. washeluting with petroleum ether/ethyl acetate (4:1 to 1:3)

Sources & evidence

ORD record
ord-683ff60f9c86478487c8731eb0ac930a
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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