Triethylamine → HCID 22992878, compound

HRID 1168622Notes

Reaction equation

HRID 1168622 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[CH2:8]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:8]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:3][CH2:6][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[CH3:8])=[O:20])=[CH:17][CH:16]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-

Product 1

HCID 22992878HCID 22992878, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of title B compound (213 mg, 1.30 mmol) in THF (6 mL) was added triethylamine 0.42 mL, 3.0 mmol). After stirring for 5 minutes, 4-hexyloxybenzoyl chloride (0.223 mL, 1.00 mmol) was added. After stirring for 4 hours, the reaction was filtered through a Celite pad. The pad was rinsed with ether (4×5 mL) and the combined filtrates were concentrated in vacuo. Purification by RP-HPLC (YMC SH-365-10 120A S-110 30×500 mm column, 40 mL/minute, 90:10 methanol/water containing 0.1% TFA)) afforded the title compound as a 1:1 mixture of cis- and trans- isomers (43 mg). MS: (ESI) (m/z) 332.

Workup

  1. stirringAfter stirring for 4 hours
  2. filtrationthe reaction was filtered through a Celite pad
  3. washThe pad was rinsed with ether (4×5 mL)
  4. concentrationthe combined filtrates were concentrated in vacuo
  5. customPurification by RP-HPLC (YMC SH-365-10 120A S-110 30×500 mm column, 40 mL/minute, 90:10 methanol/water containing 0.1% TFA))

Sources & evidence

ORD record
ord-fc9d4182977f428a991baaaeb8798a25
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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