Triethylamine → HCID 68557969, compound

HRID 20446Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N(CC)CC)C.[CH3:19][CH:20]([CH3:29])[CH2:21][C:22](=[O:28])[CH2:23][CH2:24]C(O)=O.[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:19][CH:20]([CH3:29])[CH2:21][C:22](=[O:28])[CH2:23][CH2:24][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Add benzyl chloroformate (0.712 g, 4.17 mmol), triethylamine (0.464 g, 4.59 mmol), and 4-dimethylaminopyridine (0.051 g, 0.42 mmol) to a solution of 6-methyl-4-oxo-heptanoic acid (0.66 g, 4.17 mmol) in dichloromethane (13 mL) at 0° C. Stir at 0° C. for 1 hour. Add saturated aqueous ammonium chloride (30 mL). Extract with dichloromethane (1×50 mL). Dry organic phase over magnesium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with 0-50% ethyl acetate in hexane to provide 0.87 g (84.1%) of the desired compound.

Workup

extractionExtract with dichloromethane (1×50 mL)
concentrationDry organic phase over magnesium sulfate and concentrate under reduced pressure
washSubject residue to silica gel chromatography, eluting with 0-50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-1b9c0df82eb24fa8b940031b24290300
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745438B2

Reaction notes

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