Acetic Anhydride → HCID 20773484, compound

HRID 1814984Notes

Reaction equation

HRID 1814984 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:18][C:17]2[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]([OH:26])[CH3:25])[C:14](=[O:27])[N:13]([CH3:28])[C:12]=2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:36]([O:26][C@H:24]([CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20][N:15]1[C:16](=[O:19])[C:17]2[NH:18][C:10]([CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][C:12]=2[N:13]([CH3:28])[C:14]1=[O:27])(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54535348HCID 54535348, compound

Product 1

HCID 20773484HCID 20773484, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of (R)-8-benzyloxymethyl-1-(5-hydroxyhexyl)-3-methylxanthine (19.9 g, 51.5 mmol), triethylamine (10.4 g, 103 mmol) and 4-dimethylaminopyridine (1.33 g, 11 mmol) in chloroform (130 ml) was added acetic anhydride (6.57 g, 64.4 mmol). After stirring for 3 hours at room temperature, the reaction mixture was quenched by addition of methanol (5 ml). The mixture was washed with aqueous potassium hydrogen sulfate solution (0.1 N) to pH 6-7, with water (2×50 ml) and with saturated aqueous sodium chloride solution (50 ml). After drying over magnesium sulfate, the organic solution was evaporated under reduced pressure to provide (R)-1-(5-acetoxyhexyl)-8-benzoxymethyl-3-methylxanthine (19.6 g, 88% yield) as white colored solid.

Workup

  1. customthe reaction mixture was quenched by addition of methanol (5 ml)
  2. washThe mixture was washed with aqueous potassium hydrogen sulfate solution (0.1 N) to pH 6-7, with water (2×50 ml) and with saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe organic solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae29cbcdc467440fa6191f0cea0f8d67
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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