Hydrochloric Acid → Ritonavir EP Impurity B

HRID 1457139Notes

Reaction equation

HRID 1457139 reaction equation
C(OC([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:17][C@H:18]([OH:37])[C@@H:19]([NH:27][C:28]([O:30][CH2:31][C:32]1[S:36][CH:35]=[N:34][CH:33]=1)=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@H:9]([C:13]([NH:15][C@@H:16]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:17][C@H:18]([OH:37])[C@@H:19]([NH:27][C:28]([O:30][CH2:31][C:32]1[S:36][CH:35]=[N:34][CH:33]=1)=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:14])[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2286303712-Oxa-2,7,10-triazatetradecanoic acid, 4-hydroxy-13,13-dimethyl-9-(1-methylethyl)-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl ester, [3S-(3R*,4R*,6R*,9R*)]-

Product 1

HCID 22863038Ritonavir EP Impurity B

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.1 mmol of the resultant compound of Example 31 E was treated with 10 ml of 4N HCl in dioxane, stirred at 0° C. for 1 h, concentrated in vacuo, partitioned between chloroform and aqueous NaHCO3, dried over Na2SO4, and concentrated to provide the crude desired compound.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between chloroform and aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5fd66887740b4f9db2387c3bf27dc80f
Source dataset
uspto-grants-1998_12
Patent number
US05846987

Reaction notes

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