Benzoyl chloride → HCID 18467834, compound

HRID 2229486Notes

Reaction equation

HRID 2229486 reaction equation
[CH3:1][C:2]1([C:9]([O:11]C(C)(C)C)=[O:10])[CH2:6][CH:5]([CH2:7][NH2:8])[CH2:4][O:3]1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN1CCOCC1>>[CH3:1][C:2]1([C:9]([OH:11])=[O:10])[CH2:6][CH:5]([CH2:7][NH:8][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:4][O:3]1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 79724-MethylmorpholineHCID 86758359HCID 86758359, compound

Product 1

HCID 18467834HCID 18467834, compound

Procedure

At room temperature, to a solution of 2-methyl-4-aminomethyl-2-tetrahydrofuroic acid, tert-butyl ester (30 mg, 0.139 mmole) was added benzoyl chloride (0.167 mmol, 24 mg) and N-methylmorpholine (0.334 mmol, 34 mg). After being stirred at room temperature for 2.5d, volatiles were removed and the residue was flash chromatographed through silica gel. The title compound was obtained in quantitative yield (47 mg). TLC: Rf=0.45 (1:1 hexane:ethyl acetate); Mass Spectrum: ESI m/e 320 (M+1)+.

Workup

  1. customwere removed
  2. customchromatographed through silica gel

Sources & evidence

ORD record
ord-768bfc2e984148cc854be7d39cc83168
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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