Sulfuric Acid → 188062-50-2
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+].[OH:29][S:30]([OH:33])(=[O:32])=[O:31]>C(O)(C)C>[CH2:2]1[CH:1]([NH:4][C:5]2[C:6]3[N:7]=[CH:8][N:9]([C@H:20]4[CH:21]=[CH:22][C@@H:23]([CH2:25][OH:26])[CH2:24]4)[C:10]=3[N:11]=[C:12]([NH2:14])[N:13]=2)[CH2:3]1.[CH2:2]1[CH:1]([NH:4][C:5]2[C:6]3[N:7]=[CH:8][N:9]([C@H:20]4[CH:21]=[CH:22][C@@H:23]([CH2:25][OH:26])[CH2:24]4)[C:10]=3[N:11]=[C:12]([NH2:14])[N:13]=2)[CH2:3]1.[OH:32][S:30]([OH:33])(=[O:31])=[O:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 taken in isopropanol (100 ml) and the salts were filtered off. To the filtrate, H2SO4 96% (0.78 ml, 14.0 mmol) was added dropwise. This mixture was cooled to 0-5° C. and the precipitated was filtered and dried under vacuum at 40° C. to afford 15.0 g (80%) of abacavir hemisulfate as a white powder.
Workup
- temperaturewas refluxed for 1 h
- washwashed several times with 25% solution of NaOH (10 ml)
- concentrationwas concentrated to dryness under vacuum
- filtrationthe salts were filtered off
- temperatureThis mixture was cooled to 0-5° C.
- filtrationthe precipitated was filtered
- customdried under vacuum at 40° C.
Sources & evidence
- ORD record
- ord-978d34eb58ef4bba9887224ab91114bc
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183370B2
Reaction notes
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