Sulfuric Acid → 188062-50-2

HRID 1928518Notes

Reaction equation

HRID 1928518 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+].COC(C)(C)C.[OH:35][S:36]([OH:39])(=[O:38])=[O:37]>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:38][S:36]([OH:39])(=[O:37])=[O:35]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 18651641HCID 18651641, compound

Product 1

HCID 441384188062-50-2Yield 97%

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 (6.56 g, 18.40 mmol) was slurried in a mixture of isopropanol (32.8 ml) and 10% solution of NaOH (36.1 ml, 92.0 mmol). The mixture was refluxed for 1 h. The resulting solution was cooled to 20-25° C. and tert-butyl methyl ether (32.8 ml) was added. The layers were separated and H2SO4 96% (0.61 ml, 11.03 mmol) was added dropwise to the organic layer. 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 (5.98 g, 97%) was obtained as a white powder.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customThe layers were separated
  3. temperatureThis mixture was cooled to 0-5° C.
  4. filtrationthe resulting slurry filtered off
  5. customThe solid was dried under vacuum at 40° C

Sources & evidence

ORD record
ord-d4de788e9c4e4d9cbee670c88ee73c58
Source dataset
uspto-grants-2012_05
Patent number
US08183370B2

Reaction notes

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