Methane → Hexahydrofuro[2,3-b]furan-3-yl hydrogen {4-[(4-aminobenzene-1-sulfonyl)(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl}carbonimidate--ethanol (1/1)

HRID 2175373Notes

Reaction equation

HRID 2175373 reaction equation
[CH3:1][CH:2]([CH2:4][N:5]([S:29]([C:32]1[CH:33]=[CH:34][C:35]([NH2:38])=[CH:36][CH:37]=1)(=[O:31])=[O:30])[CH2:6][C@@H:7]([OH:28])[C@@H:8]([NH:16][C:17]([O:19][C@@H:20]1[C@@H:24]2[CH2:25][CH2:26][O:27][C@@H:23]2[O:22][CH2:21]1)=[O:18])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:3].C>C(O)C>[CH3:21][CH2:20][OH:19].[CH3:3][CH:2]([CH2:4][N:5]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:6][C@@H:7]([OH:28])[C@@H:8]([NH:16][C:17]([O:19][C@@H:20]1[C@@H:24]2[CH2:25][CH2:26][O:27][C@@H:23]2[O:22][CH2:21]1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:1]

Participants

4

Reactant 2

HCID 297MethaneHCID 213039Darunavir

Product 1

HCID 23725083Hexahydrofuro[2,3-b]furan-3-yl hydrogen {4-[(4-aminobenzene-1-sulfonyl)(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl}carbonimidate--ethanol (1/1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
72.5 °C

Procedure

100 gm of darunavir was dissolved in 1000 ml of denatured ethanol (mixture of 97% ethanol and 3% toluene) at 70-75° C. to obtain clear solution. 5 gm of activated charcoal was added and stirred for 120-150 minutes. The hot solution was filtered through hyflow bed and the bed was washed with 100 ml ethanol. The solution was filtered again through 0.2μ filter maintaining temperature at 70-75° C. The reaction mass was cooled to 15-20° C., stirred for an hour and filtered. The wet cake was washed with 100 ml of chilled ethanol and dried under vacuum at 40-45° C. to afford 89.5 gm of off white colored crystalline solid.

Workup

  1. customto obtain clear solution
  2. filtrationThe hot solution was filtered through hyflow bed
  3. washthe bed was washed with 100 ml ethanol
  4. filtrationThe solution was filtered again through 0.2μ
  5. filtrationfilter
  6. temperatureThe reaction mass was cooled to 15-20° C.
  7. stirringstirred for an hour
  8. filtrationfiltered
  9. washThe wet cake was washed with 100 ml of chilled ethanol
  10. customdried under vacuum at 40-45° C.
  11. customto afford 89.5 gm of off white colored crystalline solid

Sources & evidence

ORD record
ord-e5717e8178d6425e84616da2b0ad6eb3
Source dataset
uspto-grants-2015_06
Patent number
US09062065B2

Reaction notes

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