Glycerol → Darunavir

HRID 2369456Notes

Reaction equation

HRID 2369456 reaction equation
CCO.[CH3:4][CH:5]([CH2:7][N:8]([S:32]([C:35]1[CH:36]=[CH:37][C:38]([NH2:41])=[CH:39][CH:40]=1)(=[O:34])=[O:33])[CH2:9][C@@H:10]([OH:31])[C@@H:11]([NH:19][C:20]([O:22][C@@H:23]1[C@@H:27]2[CH2:28][CH2:29][O:30][C@@H:26]2[O:25][CH2:24]1)=[O:21])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:6].OCC(CO)O>O>[CH3:6][CH:5]([CH2:7][N:8]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:9][C@@H:10]([OH:31])[C@@H:11]([NH:19][C:20]([O:22][C@@H:23]1[C@@H:27]2[CH2:28][CH2:29][O:30][C@@H:26]2[O:25][CH2:24]1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:4]

Participants

4

Reactant 2

HCID 753GlycerolHCID 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)

Product 1

HCID 213039DarunavirYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

Darunavir Ethanolate (5.0 g) was suspended into glycerol (25 g), heated to 110-120° C. under vacuum and maintained for 30 min. Water (50 mL) was added to the cooled reaction mass at 25-35° C. under stirring and the obtained suspension was stirred for 30 min at 25-35° C. The separated solid was filtered and dried at 40-45° C. under vacuum to yield 3.5 g of amorphous Darunavir.

Workup

  1. temperaturemaintained for 30 min
  2. stirringthe obtained suspension was stirred for 30 min at 25-35° C
  3. filtrationThe separated solid was filtered
  4. customdried at 40-45° C. under vacuum

Sources & evidence

ORD record
ord-cf92b1f48830463b8aab04b2077043a4
Source dataset
uspto-grants-2014_04
Patent number
US08703980B2

Reaction notes

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