Diphenyl carbonate → HCID 117599832, compound

HRID 716113Notes

Reaction equation

HRID 716113 reaction equation
[C:1]([O:9][CH2:10][C@:11]1([F:26])[C@@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([N:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][C:19]2=O)[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC(=O)OC2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+].CCOC(C)=O>CN(C=O)C.CO>[C:1]([O:9][CH2:10][C@@:11]1([F:26])[O:12][C@H:13]2[N:18]3[CH:23]=[CH:22][C:21](=[O:24])[N:20]=[C:19]3[O:17][CH:14]2[C@@H:15]1[OH:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7597Diphenyl carbonateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 117599995HCID 117599995, compound

Product 1

HCID 117599832HCID 117599832, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The benzyloxy protected 4′-fluorouridine (A3, 2.8 g, 7.6 mmol) was dissolved in DMF (10 mL). Solid diphenylcarbonate (1.80 g, 8.42 mmol, 1.1 eq) was added followed by solid sodium bicarbonate (0.36 g, 4.56 mmol 0.6 eq). The mixture was stirred and heated to 110° C. under an argon atmosphere for 8.5 hours at which time the reaction was shown to be complete by tlc (silica gel, EtOAc:MeOH=4:1). The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in methanol, and was purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane to 2:1 EtOAc:MeOH) providing the desired material in 68% yield (A4, 1.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in methanol
  3. customwas purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane to 2:1 EtOAc:MeOH)

Sources & evidence

ORD record
ord-f7b13f6a86744d1d9a10979ceb45832d
Source dataset
uspto-grants-2015_11
Patent number
US09187515B2

Reaction notes

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