Methanesulfonic Acid → Nelfinavir Mesylate

HRID 384739Notes

Reaction equation

HRID 384739 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].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].C(C(C)=O)C>C1COCC1>[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].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 6569Methyl Ethyl KetoneHCID 64143Nelfinavir

Product 1

HCID 64142Nelfinavir Mesylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Nelfinavir base (25 g) is suspended in THF (75 ml), and methanesulfonic acid (4.25 g) is added at temperature below 45° C. over 30 min. The reaction mixture is maintained at 40° C. to 45° C. for 1 hr to get clear solution. The obtained clear solution is cooled to 28° C. to 30° C. and methyl ethyl ketone (145 ml) is added over 20 min, mixed at temperature of 25° C. to 30° C. for 2 hrs. The reaction mass is cooled and maintained at 0° C. to 5° C. for 2 hrs. The precipitated solid is filtered, washed with chilled methyl ethyl ketone (12.5 ml) and dried at 90° C. to 100° C. under vacuum till becomes constant weight.

Workup

  1. temperatureThe reaction mixture is maintained at 40° C. to 45° C. for 1 hr
  2. customto get clear solution
  3. temperatureThe obtained clear solution is cooled to 28° C. to 30° C.
  4. additionmixed at temperature of 25° C. to 30° C. for 2 hrs
  5. temperatureThe reaction mass is cooled
  6. temperaturemaintained at 0° C. to 5° C. for 2 hrs
  7. filtrationThe precipitated solid is filtered
  8. washwashed with chilled methyl ethyl ketone (12.5 ml)
  9. customdried at 90° C. to 100° C. under vacuum

Sources & evidence

ORD record
ord-e27a608a4a92437a8374fcecfaca9d9f
Source dataset
uspto-grants-2013_02
Patent number
US08367832B2

Reaction notes

Loading…