Sulfuric Acid → 188062-50-2

HRID 1928521Notes

Reaction equation

HRID 1928521 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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 18651641HCID 18651641, compound

Product 1

HCID 441384188062-50-2Yield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
22.5 °C

Procedure

N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (5.0 g, 14.03 mmol) was slurried in a mixture of isopropanol (25 ml) and 10% solution of NaOH (27.5 ml, 70.1 mmol). The mixture was refluxed for 1 h. The resulting solution was cooled to 20-25° C. and the aqueous solution was discarded. The organic layer was concentrated to dryness. isopropanol (10 ml) was added and further concentrated to dryness two times. To this residue, isopropanol (25 ml) was added and the salts were filtered off. To the obtained solution, H2SO4 96% (0.39 ml, 7.0 mmol) was added dropwise. This mixture was cooled to 0-5° C. and the resulting slurry filtered off. The solid was dried under vacuum at 40° C. Abacavir hemisulfate (3.7 g, 79%) was obtained as a white powder.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. concentrationThe organic layer was concentrated to dryness
  3. additionisopropanol (10 ml) was added
  4. concentrationfurther concentrated to dryness two times
  5. additionTo this residue, isopropanol (25 ml) was added
  6. filtrationthe salts were filtered off
  7. temperatureThis mixture was cooled to 0-5° C.
  8. filtrationthe resulting slurry filtered off
  9. customThe solid was dried under vacuum at 40° C

Sources & evidence

ORD record
ord-856ab06bbdd9420b8c44be151ab33ad9
Source dataset
uspto-grants-2012_05
Patent number
US08183370B2

Reaction notes

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