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Sodium ethoxide → (S)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-ethoxy-4-chloro-5-isoquinolinesulfonyl)pyrrolidine

HRID 2425435
Notes
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Reaction equation

HRID 2425435 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([Cl:29])=[CH:21][N:22]=[C:23](Cl)[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:17])=[O:16])[CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-:30][CH2:31][CH3:32].[Na+]>C(O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]([C@H:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([Cl:29])=[CH:21][N:22]=[C:23]([O:30][CH2:31][CH3:32])[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:16])=[O:17])[CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 866278123-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1,4-dichloro-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67242702(S)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-ethoxy-4-chloro-5-isoquinolinesulfonyl)pyrrolidineYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 57417360
Sodium chloride; water
Solvent

Conditions

Temperature
50 °C

Procedure

A solution of Intermediate 25 (230 mg) obtained in Example 36-1 in ethanol (10 ml) was added with sodium ethoxide (204 mg, Aldrich), and the mixture was stirred at 50° C. for 12 hours. The reaction mixture was added with saturated brine (10 ml), and extracted three times with ethyl acetate (10 ml for each time), and the combined organic layer was washed with saturated brine (20 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (223 mg).

Workup

  1. extractionextracted three times with ethyl acetate (10 ml for each time), and the combined organic layer
  2. washwas washed with saturated brine (20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-13d0baca8f6a43618322a310eb3a142d
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07964613B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes