Triphenylphosphine → HCID 67814681, compound

HRID 1024657Notes

Reaction equation

HRID 1024657 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]4[C@@H:18]([CH2:26]O)[O:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:65][NH:66][S:67]([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][C:71]=1[N+:76]([O-:78])=[O:77])(=[O:69])=[O:68]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:24])([CH3:25])[O:23][C@@H:19]4[C@@H:18]([CH2:26][N:66]([CH3:65])[S:67]([C:70]4[CH:75]=[CH:74][CH:73]=[CH:72][C:71]=4[N+:76]([O-:78])=[O:77])(=[O:68])=[O:69])[O:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 264906N-methyl-2-nitrobenzene-1-sulfonamideHCID 67776590HCID 67776590, compound

Product 1

HCID 67814681HCID 67814681, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ((3aR,4R,6R,6aR)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (1.52 g, 3.33 mmol) and triphenylphosphine (1.92 g, 7.32 mmol) in tetrahydrofuran (25 mL) was cooled at 0° C. and treated dropwise with diethyl azodicarboxylate (1.26 mL, 7.99 mmol). The now yellow solution was treated dropwise with a solution of N-methyl-2-nitrobenzenesulfonamide (1.01 g, 4.66 mmol) in tetrahydrofuran (9.9 mL, 120 mmol) over ˜5 minutes and the solution was allowed to stir and slowly warm up to room temperature. After 24 h at room temperature, HPLC indicated that the starting material had been consumed. The reaction mixture was partially concentrated and the solution was purified by flash chromatography (175 g silica gel, 60-90% EA/hept) to yield the title compound (0.82 g, 38%) as a light yellow glass: MS (ESI+) for C30H34N6O9S m/z 655.3 (M+H)+; (ESI−) for C30H34N6O9S m/z 653.3 (M−H)−; HPLC purity 68% (ret. time, 3.94 min).

Workup

  1. customhad been consumed
  2. concentrationThe reaction mixture was partially concentrated
  3. customthe solution was purified by flash chromatography (175 g silica gel, 60-90% EA/hept)

Sources & evidence

ORD record
ord-60c1a85023b84f558df7c00c9722b168
Source dataset
uspto-grants-2014_05
Patent number
US08722877B2

Reaction notes

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