Hydrogen chloride-ethyl acetate → 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide hydrochloride

HRID 1754308Notes

Reaction equation

HRID 1754308 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13]([O:15][C@H:16]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[C:29]([O:37][CH2:38][CH:39]2[CH2:41][CH2:40]2)[CH:28]=1)[CH2:17][C:18]1[C:23]([Cl:24])=[CH:22][N+:21]([O-:25])=[CH:20][C:19]=1[Cl:26])=[O:14])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[ClH:24].[Cl:26][C:19]1[CH:20]=[N+:21]([O-:25])[CH:22]=[C:23]([Cl:24])[C:18]=1[CH2:17][C@@H:16]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[C:29]([O:37][CH2:38][CH:39]2[CH2:41][CH2:40]2)[CH:28]=1)[O:15][C:13]([C@H:9]1[NH:8][CH2:12][CH2:11][S:10]1)=[O:14]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 867202674-((S)-2-((S)-3-(tert-butoxycarbonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

Product 1

HCID 710925203,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide hydrochlorideYield 168.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-((S)-2-((S)-3-(tert-butoxycarbonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (4.22 g, 6.64 mmol) was dissolved in ethyl acetate (10 ml). HCl/ethyl acetate 4.2 M (50 ml) was added, and the reaction was stirred at RT for 5 minutes. A white precipitate formed, and it was filtered, washed with ethyl acetate (2×) and hexane and dried in the vacuum oven to yield 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide hydrochloride (3.19 g, 5.6 mmol, 84% Yield)

Workup

  1. customA white precipitate formed
  2. filtrationit was filtered
  3. washwashed with ethyl acetate (2×) and hexane
  4. customdried in the vacuum oven

Sources & evidence

ORD record
ord-6c79805f21c04cf1a9d2e971a6d2da71
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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