Sodium Hydroxide → Abacavir

HRID 420887Notes

Reaction equation

HRID 420887 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>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

5

Reactant 3

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

Product 1

HCID 441300AbacavirYield 77.3%

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 (1.0 g, 2.80 mmol) was slurried in a mixture of isopropanol (2 ml) and 10% solution of NaOH (1.1 ml, 2.80 mmol). The mixture was refluxed for 1 h. The resulting solution was cooled to 20-25° C. and tert-butyl methyl ether (2 ml) was added. The aqueous layer was discarded, the organic phase was cooled to 0-5° C. and the resulting slurry filtered off. The solid was dried under vacuum at 40° C. Abacavir (0.62 g, 77%) was obtained as a white powder.

Workup

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

Sources & evidence

ORD record
ord-4626d27f57e84879aa9e3a6bd3ec986b
Source dataset
uspto-grants-2012_01
Patent number
US08097723B2

Reaction notes

Loading…