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

HRID 2284829
Notes
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Reaction equation

HRID 2284829 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>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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 8857
Ethyl Acetate
Solvent
2×

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 in ethyl acetate (50 mL, 4.2 M, 210 mmol) was added, and the reaction was stirred at room temperature for 5 minutes. A white precipitate formed, and it was filtered, washed with Ethyl Acetate (2×) and hexane, and dried in a 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%)

Workup

  1. customA white precipitate formed
  2. filtrationit was filtered
  3. washwashed with Ethyl Acetate (2×) and hexane
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4ab0b217823b45528d7857ac8986bdca
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145409B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes