Sulfuric Acid → HCID 86601659, compound

HRID 1895514Notes

Reaction equation

HRID 1895514 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: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:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])[CH3:3].[S:52](=[O:56])(=[O:55])([OH:54])[OH:53].CC([C@H](NC(OC)=O)C(N[C@H]([C@@H](O)CN(NC([C@@H](NC(OC)=O)C(C)(C)C)=O)CC1C=CC(C2C=CC=CN=2)=CC=1)CC1C=CC=CC=1)=O)(C)C.OS(O)(=O)=O.CCCCCCC>C(O)C.C1(C)C=CC=CC=1.CCCCCC>[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:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:1])[CH3:3].[S:52](=[O:54])(=[O:53])([OH:56])[O-:55]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 8900HeptaneHCID 148192AtazanavirHCID 158550Atazanavir Sulfate

Product 1

HCID 86601659HCID 86601659, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

The Form E3 is prepared by slurrying atazanavir free base in ethanol, treating the slurry with concentrated sulfuric acid employing a molar ratio of acid: free base with the range from about 1:1 to about 1.1:1, heating the resulting solution at from about 30 to about 40° C., seeding the solution with ethanol wet E3 crystals of atazanavir sulfate, treating the mixture with heptane (or other solvent such as hexane or toluene), filtering, and drying to yield atazanavir bisulfate Form E3 (triethanol solvate).

Workup

  1. temperaturefree base with the range from about 1:1 to about 1.1:1, heating the resulting solution at from about 30 to about 40° C.
  2. filtrationfiltering
  3. customdrying

Sources & evidence

ORD record
ord-73052e0c5d7d459aa4077f9569d60fa8
Source dataset
uspto-grants-2013_08
Patent number
US08513428B2

Reaction notes

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