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Hydrochloric Acid → Des((2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl)ritonavir

HRID 1457139
Notes
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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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22863037(2S,3S,5S)-5-(N-(N-(t-butyloxycarbonyl) valinyl)amino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

Product 1

HCID 22863038Des((2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl)ritonavir

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05846987

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes