Triethylamine → HCID 68613368, compound

HRID 1877323Notes

Reaction equation

HRID 1877323 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:22][CH3:23])CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:12]1[C:13](=[O:16])[CH2:14][CH2:15][CH:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:10])[CH2:2][CH2:3][CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10847460555-57-9

Product 1

HCID 68613368HCID 68613368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a stirring solution of 5.5 g of 5-Oxo-pyrrolidine-2-carboxylic acid benzyl ester (25 mmol), 4 mL of triethylamine, 3.3 g of N,N-dimethylaminopyridine (27 mmol) in 40 mL of dichloromethane, was added 4.1 g of 4-pentenyl-1-yl chloroformate (27.6 mmol). The reaction mixture was then warmed to rt, and stirred over weekend. After concentration, the resulting residue was dissolved in ethyl ether 120 mL, washed with 30 mL of 1.0 N aq. HCl, brine subsequently, dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure, and the residue was purified by flash chromatography on silica gel using heptane/EtOAc (v/v 1/1), giving 7.3 g of colorless oil as intermediate 17-2 (88%). LC-MS: m/z=331.2 (ES+).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe resulting residue was dissolved in ethyl ether 120 mL
  3. washwashed with 30 mL of 1.0 N aq. HCl, brine subsequently
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-de85703c8ee94d8e8ba1a3505d2a8a69
Source dataset
uspto-grants-2012_11
Patent number
US08309685B2

Reaction notes

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