Triphenylphosphine → HCID 86602836, compound

HRID 644948Notes

Reaction equation

HRID 644948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C@@H:11](O)[CH2:10][C@H:9]2[C:14]([N:16]2[CH2:21][CH2:20][C:19]([CH2:28][N:29]3[C:33]([CH3:35])([CH3:34])[CH2:32][O:31][C:30]3=[O:36])([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])=[CH:4][CH:3]=1.[CH3:37][NH:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][C:43]=1[N+:51]([O-:53])=[O:52])(=[O:41])=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C@H:9]([C:14]([N:16]3[CH2:17][CH2:18][C:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)([CH2:28][N:29]4[C:33]([CH3:34])([CH3:35])[CH2:32][O:31][C:30]4=[O:36])[CH2:20][CH2:21]3)=[O:15])[CH2:10][C@@H:11]([N:38]([CH3:37])[S:39]([C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][C:43]=3[N+:51]([O-:53])=[O:52])(=[O:41])=[O:40])[CH2:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12669759HCID 12669759, compoundHCID 68520987HCID 68520987, compound

Product 1

HCID 86602836HCID 86602836, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A 25 mL round bottom flask equipped with a magnetic stir bar was charged with 0.103 g (0.20 mmol) of the product of Step F, 0.073 g (0.28 mmol) of N-methyl-2,4-dinitrobenzenesulfonamide and 0.157 g (0.60 mmol) of triphenylphosphine. The solids were dissolved in 2 mL of benzene, and the atmosphere in the flask was evacuated and purged with nitrogen. The reaction mixture was stirred and cooled to 0° C. with an external ice-water bath and then 95 μL (0.60 mmol) of diethyl azodicarboxylate was added. The reaction mixture was allowed to warm to room temperature and was stirred an additional 1 h at which point TLC analysis (75% ethyl acetate-hexanes) indicated consumption of the starting material. The reaction mixture was then evaporated in vacuo and the residue was purified on a Biotage Flash 40i chromatography apparatus (40 g Flash 40S silica gel cartridge) eluted with 50% ethyl acetate-hexanes. Evaporation of the purified fractions and drying in vacuo afforded the title compound as an amorphous yellow solid.

Workup

  1. customA 25 mL round bottom flask equipped with a magnetic stir bar
  2. customthe atmosphere in the flask was evacuated
  3. custompurged with nitrogen
  4. temperatureto warm to room temperature
  5. customconsumption of the starting material
  6. customThe reaction mixture was then evaporated in vacuo
  7. customthe residue was purified on a Biotage Flash 40i chromatography apparatus (40 g Flash 40S silica gel cartridge)
  8. washeluted with 50% ethyl acetate-hexanes
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-84655a5a538441c6bc11609f35f56d76
Source dataset
uspto-grants-2010_04
Patent number
US07700778B2

Reaction notes

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