Triethylamine → HCID 131730205, compound

HRID 386606Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH:22]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:22]([C:11](=[O:13])[C:10]([CH3:15])([CH3:14])[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:34]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-(benzyloxy)-2,2-dimethylpropanoic acid from Step B (415 mg, 1.99 mmol) in DCM (20 mL) was added one drop of DMF (cat.) followed by the drop wise addition of oxalyl chloride (329 mg, 2.59 mmol) over 10 minutes, while at ambient temperature. After the evolution of gas has ceased, the reaction was cooled to 0° C., prior to the introduction of ethyl anilinoacetate (429 mg, 2.39 mmol) and triethylamine (302 mg, 2.99 mmol). After 2 hours at 0° C., the reaction was allowed to warm to ambient temperature and then stir for an additional 1 hour. The reaction mixture was applied directly to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99.5:0.5 to 98:2. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=370 (M+1).

Workup

temperatureto warm to ambient temperature
customThe reaction mixture was applied directly to a silica gel column for purification
washeluting with a gradient of CH2Cl2
additionProduct containing fractions
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7a64c76e39c7430ab9a8d607242e55e3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372859B2

Reaction notes

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