Methanol → Nelfinavir Mesylate

HRID 395907Notes

Reaction equation

HRID 395907 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:11][C@H:12]([C@H:21]([OH:40])[CH2:22][N:23]1[C@H:32]([C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][C@H:30]2[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24]1)[CH2:13][S:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10].CO.[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>C(OCC)C.C(OC)(C)(C)C.C1COCC1.C(O)C>[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:11][C@H:12]([C@H:21]([OH:40])[CH2:22][N:23]1[C@H:32]([C:33]([NH:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:31][C@H:30]2[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24]1)[CH2:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]

Participants

8

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 64143Nelfinavir

Product 1

HCID 64142Nelfinavir Mesylate

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Nelfinavir free base is slurried or dissolved in a suitable solvent (such as THF, methanol, or ethanol). THF is the preferred solvent. A molar equivalent amount of methanesulfonic acid is added, and the mixture is stirred until all solids dissolve. The solution is added to several volumes of an antisolvent (such as methyl t-butyl ether, diethyl ether, hexanes, or heptanes) that is rapidly stirring. Diethyl ether is the preferred antisolvent. After stirring, the mixture is filtered and washed with antisolvent. The solid is dried in a vacuum oven to yield nelfinavir mesylate.

Workup

  1. dissolutiondissolve
  2. stirringis rapidly stirring
  3. stirringAfter stirring
  4. filtrationthe mixture is filtered
  5. washwashed with antisolvent
  6. customThe solid is dried in a vacuum oven

Sources & evidence

ORD record
ord-a717eb657323476e86658e99be4fecdd
Source dataset
uspto-grants-2003_08
Patent number
US06605721B2

Reaction notes

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