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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2175373Generated: October 30, 2026

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)

https://huagongshe.com/reaction/2175373

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethaneHCID 297—
ReactantDarunavirHCID 213039—
SolventEthanolHCID 702—
ProductHexahydrofuro[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)HCID 23725083—

Reaction Conditions

Temperature72.5 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09062065B2
Source datasetuspto-grants-2015_06
ORD IDord-e5717e8178d6425e84616da2b0ad6eb3
Source noteuspto-grants-2015_06