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Hydrochloric Acid → (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627265
Notes
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Reaction equation

HRID 627265 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][CH3:33])[CH:20]=[C:19]1[C:34](=[O:37])[NH:35][CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].Cl>O1CCOCC1>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:34]([NH:35][CH3:36])=[O:37])=[CH:20][C@@H:21]([CH2:31][O:32][CH3:33])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89852105(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(methoxymethyl)-4-(methylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89852470(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Procedure

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(methoxymethyl)-4-(methylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 256, 1 g, 1.85 mmol) in dioxane (10 ml) at room temperature was added 4M HCl in Dioxane (2 ml, 57.16 mmol). The reaction mixture was stirred at that temperature for 4-5 hours. The reaction mixture was concentrated and the crude was taken up in 2M NaOH and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Silica gel chromatography (increasing percentage of methanol in dichloromethane) afforded the title compound as a thick oil (0.56 g, 69%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureSilica gel chromatography (increasing percentage of methanol in dichloromethane)

Sources & evidence

ORD record
ord-1c621a2215d944bb848a267f6a40a771
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309245B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes