Sodium Hydroxide → Abacavir

HRID 1928525Notes

Reaction equation

HRID 1928525 reaction equation
[CH:1]1([NH:4][C:5]2[N:13]=[C:12]([NH:14]C(=O)C(C)C)[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@@H:20]2[CH2:24][C@H:23]([CH2:25][OH:26])[CH:22]=[CH:21]2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)(C)C>[CH:8]1[N:9]([C@H:20]2[CH:21]=[CH:22][C@@H:23]([CH2:25][OH:26])[CH2:24]2)[C:10]2[N:11]=[C:12]([NH2:14])[N:13]=[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18651641HCID 18651641, compound

Product 1

HCID 441300AbacavirYield 43%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (1.25 g, 3.51 mmol) was slurried in a mixture of isopropanol (2.5 ml) and 10% solution of NaOH (1.37 ml, 3.51 mmol). The mixture was refluxed for 1 h and concentrated to dryness. The residue was crystallized in acetonitrile. Abacavir (0.43 g, 43%) was obtained as a white powder.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. concentrationconcentrated to dryness
  3. customThe residue was crystallized in acetonitrile

Sources & evidence

ORD record
ord-877f7e5cd38f461f9ccdcddf439c8456
Source dataset
uspto-grants-2012_05
Patent number
US08183370B2

Reaction notes

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