Triphenylphosphine → HCID 23434069, compound

HRID 1004180Notes

Reaction equation

HRID 1004180 reaction equation
O[CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([O:44][C:45]([NH:47][O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[C:40]([O:44][C:45]([N:47]([CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 5462977Diethyl azodicarboxylateHCID 23434113HCID 23434113, compound

Product 1

HCID 23434069HCID 23434069, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-hydroxymethyl-2,5-di(4-pyridyl)-4-methylthiophene (0.282 g), triphenylphosphine(0.446 g), and N,O-di-(tert-butoxycarbonyl)hydroxylamine (0.224 g), in THF (20 mL) was added diethylazodicarboxylate (0.296 g) under nitrogen. After stirring for 23 hours, the reaction mixture was poured into water (50 mL) and the whole was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2 -MeOH (1:1:0.04). The resulting product was purified by column chromatography on silica(NH-silica gel, FUJI SILISIA CHEMICAL LTD. DM203 5)(ethyl acetate-CH2Cl2 --MeOH=1:1:0.04) to give the subtitle compound (0.17 g)

Workup

  1. extractionthe whole was extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate-CH2Cl2 -MeOH (1:1:0.04)
  7. customThe resulting product was purified by column chromatography on silica(NH-silica gel, FUJI SILISIA CHEMICAL LTD. DM203 5)(ethyl acetate-CH2Cl2 --MeOH=1:1:0.04)

Sources & evidence

ORD record
ord-c88815f3437048b3866b77d0f3a83321
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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