Ethanol → Atazanavir Sulfate

HRID 1257099Notes

Reaction equation

HRID 1257099 reaction equation
[CH3:1][C:2]([C@H:5]([NH:47][C:48]([O:50][CH3:51])=[O:49])[C:6]([NH:8][C@H:9]([C@@H:17]([OH:46])[CH2:18][N:19]([NH:33][C:34]([C@@H:36]([NH:41][C:42]([O:44][CH3:45])=[O:43])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])[CH3:3].CCO.[S:55](=[O:59])(=[O:58])([OH:57])[OH:56]>CC#N>[CH3:4][C:2]([C@H:5]([NH:47][C:48]([O:50][CH3:51])=[O:49])[C:6]([NH:8][C@H:9]([C@@H:17]([OH:46])[CH2:18][N:19]([NH:33][C:34]([C@@H:36]([NH:41][C:42]([O:44][CH3:45])=[O:43])[C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:32]=2)=[CH:25][CH:26]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:1])[CH3:3].[OH:58][S:55]([OH:59])(=[O:57])=[O:56]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 148192Atazanavir

Product 1

HCID 158550Atazanavir SulfateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 mL sample viral equipped with a magnetic stir was charged atazanavir base (1.0 g), 99.5% EtOH (mL, 1 vol), and MeCN (4 mL, 4 vol) at 20-30° C. Concentrated sulfuric acid (0.085 mL, 1.1 equiv) was added at 20-30° C., and the resulting clear amber solution was stirred at 20-30° C. for 4 hr. The product was filtered, washed with a mixture of EtOH/MeCN (1:4, 5 mL, 5 vol), and dried under vacuum at 40-50° C. for 16 hr to afford atazanavir sulfate in Form A (0.47 g, 42% yield, 99.9% HPLC purity).

Workup

  1. customTo a 20 mL sample viral equipped with
  2. stirringthe resulting clear amber solution was stirred at 20-30° C. for 4 hr
  3. filtrationThe product was filtered
  4. washwashed with a mixture of EtOH/MeCN (1:4, 5 mL, 5 vol)
  5. customdried under vacuum at 40-50° C. for 16 hr

Sources & evidence

ORD record
ord-a97e775771cd4d929cd1bfd1268eef7e
Source dataset
uspto-grants-2013_06
Patent number
US08461347B2

Reaction notes

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