Acetic Acid → 3-Acetoxymethyl-1-benzyl-7-benzyloxy-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734534Notes

Reaction equation

HRID 1734534 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([CH2:25][OH:26])=[C:9]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:43](O)(=[O:45])[CH3:44].C(=O)([O-])O.[Na+]>O1CCCC1.O>[C:43]([O:26][CH2:25][C:10]1[C:11]2[C:12](=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:14]=[N:15][CH:16]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]=1[CH3:27])(=[O:45])[CH3:44]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 194377811-Benzyl-7-benzyloxy-3-hydroxymethyl-2-methylpyrrolo[2,3-d]pyridazine

Product 1

HCID 194377603-Acetoxymethyl-1-benzyl-7-benzyloxy-2-methylpyrrolo[2,3-d]pyridazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.65 g (4.59 mmol) of 1-benzyl-7-benzyloxy-3-hydroxymethyl-2-methylpyrrolo [2,3-d]pyridazine, 3.8 g (18.6 mmol) of dicyclohexylcarbodiimide and 1.6 ml (27.4 mmol) of glacial acetic acid in 50 ml of anhydrous tetrahydrofuran is stirred at room temperature for 18 h. The solution is then treated with 50 ml of water, rendered neutral with saturated sodiumhydrogen carbonate solution and extracted with 3×50 ml of dichloromethane. The organic extracts are washed with 50 ml of water, dried over magnesium sulfate and concentrated. The residue which remains is chromatographed on silica gel (eluent: ethyl acetate). After crystallization from diisopropyl ether, 1.3 g (71%) of the title compound are isolated. M.p.: 121°-122° C.

Workup

  1. extractionextracted with 3×50 ml of dichloromethane
  2. washThe organic extracts are washed with 50 ml of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue which remains is chromatographed on silica gel (eluent: ethyl acetate)
  6. customAfter crystallization from diisopropyl ether, 1.3 g (71%) of the title compound
  7. customare isolated

Sources & evidence

ORD record
ord-6a45e5ebeb0a4c649b76dfd8b2ba3000
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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