Triethylamine → HCID 59773024, compound

HRID 2220690Notes

Reaction equation

HRID 2220690 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19].C([N:30]([CH2:33]C)[CH2:31][CH3:32])C.[C:35](=[O:38])(O)[O-].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:33][N:30]([CH2:31][C:32]1[O:38][C:35]2[CH:21]=[CH:22][CH:23]=[CH:15][C:16]=2[CH:17]=1)[C:18](=[O:19])[C:17]1[CH:16]=[C:15]([O:14][CH3:13])[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 643455N-Boc-pyrrolidine

Product 1

HCID 59773024HCID 59773024, compound

Procedure

2-(S)-{[Benzofuran-2-ylmethyl]-amino]-methyl}-pyrrolidin-1-carboxylic acid tert-butyl ester 0.33 g (0.28 mmol), 3,4,5-trimethoxy-benzoyl chloride 65 mg (0.28 mmol) and triethylamine 0.04 mL (0.28 mmol). After 1 hour, saturated sodium bicarbonate added and the mixture extracted with dichloromethane, combined organic layer, dried over magnesium sulfate, filtered, and concentrated under vacuum. Purification over silica gel chromatography, elution ethyl acetate-hexane 5.5-4.5, gave 100 mg of light yellow oil.

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification
  6. washover silica gel chromatography, elution ethyl acetate-hexane 5.5-4.5

Sources & evidence

ORD record
ord-9af395e3932642eaabc27efcab7cedcc
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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