Sulfuric Acid → 188062-50-2

HRID 1928520Notes

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

Conditions

Temperature: 22.5 °C

Procedure

To a solution of N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl) cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (1.0 g, 2.80 mmol) in isopropanol (10 ml) a 10% solution of NaOH (5.5 ml, 14.03 mmol) was added. The mixture was refluxed for 1 h. The resulting solution was cooled to 20-25° C. and the aqueous layer was separated. H2SO4 96% (0.07 ml, 1.22 mmol) was added dropwise to the organic layer. The mixture was concentrated to half volume and the salts were filtered off. To the obtained solution, H2SO4 96% (0.07 ml, 1.22 mmol) was added dropwise and cooled to 0-5° C. The solid was filtered off and dried under vacuum at 40° C. Abacavir hemisulfate (0.56 g, 60%) was obtained as a white powder.

Workup

temperatureThe mixture was refluxed for 1 h
customthe aqueous layer was separated
concentrationThe mixture was concentrated to half volume
filtrationthe salts were filtered off
temperaturecooled to 0-5° C
filtrationThe solid was filtered off
customdried under vacuum at 40° C

Sources & evidence

ORD record: ord-162398a877cd4f8fbb0343a53ab13c1a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183370B2

Reaction notes

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