Heptane → Darunavir

HRID 2369455Notes

Reaction equation

HRID 2369455 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].CCCCCCC>C(OCC)(=O)C>[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 8900HeptaneHCID 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 86.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
42.5 °C

Procedure

Darunavir Ethanolate (10 g) was dissolved in ethyl acetate (50 mL). The solution was heated to 40-45° C. and maintained for 30 min. Ethyl acetate was distilled off under vacuum completely to get residue in the form of semisolid. n-Heptane (50 mL) was added to the residue and stirred for 30 min. at ambient temperature. The separated solid was filtered, washed the wet cake with n-heptane (5 mL) and dried at 40-45° C. under vacuum to get 8.0 g of amorphous Darunavir.

Workup

  1. temperaturemaintained for 30 min
  2. distillationEthyl acetate was distilled off under vacuum completely
  3. customto get residue in the form of semisolid
  4. filtrationThe separated solid was filtered
  5. washwashed the wet cake with n-heptane (5 mL)
  6. customdried at 40-45° C. under vacuum

Sources & evidence

ORD record
ord-b5081a73071c4491891046f46c9a270d
Source dataset
uspto-grants-2014_04
Patent number
US08703980B2

Reaction notes

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