Sodium Hydroxide → Abacavir

HRID 1928526Notes

Reaction equation

HRID 1928526 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 90%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (10 g, 28 mmol), isopropanol (100 ml) and 10% solution of NaOH (16.8 ml, 42 mmol) was refluxed for 1 h. The resulting solution was cooled to 20-25° C. and washed several times with 25% solution of NaOH (10 ml). The wet organic layer was neutralized to pH 7.0-7.5 with 17% hydrochloric acid and it was concentrated to dryness under vacuum. The residue was crystallized in ethyl acetate (150 ml) to afford abacavir (7.2 g, 90%).

Workup

  1. temperaturewas refluxed for 1 h
  2. washwashed several times with 25% solution of NaOH (10 ml)
  3. concentrationwas concentrated to dryness under vacuum
  4. customThe residue was crystallized in ethyl acetate (150 ml)

Sources & evidence

ORD record
ord-e9f210aa35a34e98b4764400cff2383a
Source dataset
uspto-grants-2012_05
Patent number
US08183370B2

Reaction notes

Loading…