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Sulfuric Acid → Z-Pyr-OtBu

HRID 1620448
Notes
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Reaction equation

HRID 1620448 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:25]=[C:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[O:16]=[C:15]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@H:12]([C:17]([O:19][C:26]([CH3:28])([CH3:27])[CH3:25])=[O:18])[CH2:13][CH2:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 10340Sodium CarbonateHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Product 1

HCID 10615573Z-Pyr-OtBuYield 67%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

100 g of (S)-1-(benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid was dissolved in dehydrated dichloromethane (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and 213 g of isobutene were added, followed by stirring overnight at +20° C. or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67%). Enantiomeric excess: 99.9% ee or more (CHIRALPAK AD-H, 4.6×150 mm, UV 210 nm, hexane/ethanol=2/1, flow rate 1 mL/min., retention time 4.2 min.).

Workup

  1. customfollowed by liquid separation of the organic phase
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customcrystallized with hexane/ethyl acetate

Sources & evidence

ORD record
ord-cf93b57f3ed24541b9996e2450fc07cb
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772490B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes