Triphenylphosphine → CID 66550531

HRID 335493Notes

Reaction equation

HRID 335493 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([CH2:13]O)[C@@H:10]([OH:15])[C@H:9]([OH:16])[C@H:7]2[N:8]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC(/N=N\C(OC(C)C)=O)=O)(C)C.P([N:67]=[N+:68]=[N-:69])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>O1CCCC1>[N:67]([CH2:13][C@H:11]1[O:12][C@H:6]2[C@H:7]([N:8]=[C:4]([NH:3][CH2:1][CH3:2])[S:5]2)[C@@H:9]([OH:16])[C@@H:10]1[OH:15])=[N+:68]=[N-:69]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 24808478Thiamet G, >=98% (HPLC)HCID 178459212HCID 178459212, compound

Product 1

HCID 66550531CID 66550531Yield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 2.5 mL seal vial equipped with a stir bar was added (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (150.00 mg; 0.60 mmol; 1.00 eq.) in tetrahydrofuran (2.00 ml) followed by triphenylphosphine (316.90 mg; 1.21 mmol; 2.00 eq.), isopropyl(Z)-(isopropoxyacetyl)diazenecarboxylate (0.25 ml; 1.21 mmol; 2.00 eq.). Diphenyl azidophosphate (0.26 ml; 1.21 mmol; 2.00 eq.) was then added dropwise in 15 min. During the addition, the former obtained green-yellow clear solution slowly turned to turbid and finally became clear again. The mixture was stirred at room temperature for 48 h. The mixture was purified via Yamazen channel 2 and lyophilized to provide 134.6 mg (81%) of the title compound as white solid.

Workup

  1. customIn a 2.5 mL seal vial
  2. customequipped with a stir bar
  3. additionDuring the addition
  4. customThe mixture was purified via Yamazen channel 2

Sources & evidence

ORD record
ord-5bc2ae342855411f916110293a932262
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

Loading…