HCID 10903732, compound → Lamivudine

HRID 1075559

Reaction equation

HRID 1075559 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]2[O:12][C@@H:11]([CH2:13][O:14]C(=O)C3C=CC=CC=3)[S:10][CH2:9]2)[C:4](=[O:23])[N:3]=1>CO>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]2[O:12][C@@H:11]([CH2:13][OH:14])[S:10][CH2:9]2)[C:4](=[O:23])[N:3]=1

Participants

3

Reactant 1

HCID 10903732HCID 10903732, compound2×

Product 1

HCID 60825LamivudineYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (cis)-4-amino-1-(2-benzoyloxymethyl-1,3-oxathiolan-5-yl)(1H)-pyrimidin-2-one (Intermediate 3) (8.19 g) and Amberlite IRA-400 (OH) resin (8.24 g) in methanol (250 ml) was stirred and heated to reflux for 11/4 h. Solids were removed by filtration then washed with methanol. The combined filtrates were evaporated. The residue was triturated with ethyl acetate (80 ml). The resulting white solid was collected by filtration to give the title product (5.09 g), 1H NMR (DMSO-d6) 3.04 (1H), 3.40 (1H), 3.73 (2H), 5.18 (1H), 5.29 (1H), 5.73 (1H), 6.21 (1H), 7.19 (2H), 7,81 (1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 11/4 h
  3. customSolids were removed by filtration
  4. washthen washed with methanol
  5. customThe combined filtrates were evaporated
  6. customThe residue was triturated with ethyl acetate (80 ml)
  7. filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-c9cce1c6c73d40baa1fedc1e1bd85be0
Source dataset
uspto-grants-1999_05
Patent number
US05905082

Linked notes

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