Acetic Anhydride → [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-anilino-6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetate

HRID 1578355Notes

Reaction equation

HRID 1578355 reaction equation
[C:1]1([NH:7][C:8]2[N:9]=[C:10]([OH:26])[C:11]3[N:12]=[CH:13][N:14]([C:24]=3[N:25]=2)[C@@H:15]2[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[C@H:16]2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:31](=[O:33])[CH3:32])(=O)C>N1C=CC=CC=1>[C:1]1([NH:7][C:8]2[N:9]=[C:10]([OH:26])[C:11]3[N:12]=[CH:13][N:14]([C:24]=3[N:25]=2)[C@@H:15]2[O:23][C@H:20]([CH2:21][O:22][C:31](=[O:33])[CH3:32])[C@@H:18]([O:19][C:18](=[O:19])[CH3:20])[C@H:16]2[O:17][C:16](=[O:17])[CH3:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178521067HCID 178521067, compound

Product 1

HCID 178476359[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-anilino-6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 100 parts by volume of pyridine is suspended 10 parts by weight of 2-phenylaminoinosine and 50 parts by weight of acetic anhydride is added dropwise. The mixture is stirred for 3 hours, at the end of which time it is concentrated under reduced pressure. The residue is recrystallized from 5 parts by volume of methanol. The procedure gives 2 parts by weight of 2-phenylamino-2',3',5'-tri-O-acetylinosine in the form of colorless flocs.

Workup

  1. additionis added dropwise
  2. concentrationis concentrated under reduced pressure
  3. customThe residue is recrystallized from 5 parts by volume of methanol

Sources & evidence

ORD record
ord-d68a2aaddcc841028ba5ed5cd0197d3b
Source dataset
uspto-grants-1976_02
Patent number
US03936439

Reaction notes

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