Triethylamine → HCID 69070340, compound

HRID 1876928Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[CH:7]([NH:17][C:18](=[O:28])[C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=1[CH3:27])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[CH:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:30][CH2:31][O:32][C:33](/[C:35](/Cl)=[N:36]\[OH:37])=[O:34].CCN(CC)CC.C(OCC)(=O)C>C(Cl)Cl>[CH2:31]([O:32][C:33]([C:35]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH:7]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:29])[NH:17][C:18](=[O:28])[C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[CH:14][CH:13]=2)[O:37][N:36]=1)=[O:34])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

195 mg (0.498 mmol) of (3) and 377 mg (2.49 mmol) of ethyl chlorooximido acetate were dissolved in 4 ml of DCM and cooled to 0° C. 417 μl (2.99 mmol) of Et3N dissolved in 4 ml of DCM were added slowly (1 drop/7 seconds). After 3 h additional 3 eq. of ethyl chlorooximidoacetate and Et3N were added. The reaction mixture was poured into ethyl acetate, washed with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed at the evaporator. The product was purified by column chromatography on silica gel using ethyl acetate/hexane to give 165 mg of (4).

Workup

additionwere added slowly (1 drop/7 seconds)
washwashed with saturated NaHCO3, brine
dry with materialdried over Na2SO4
customThe solvent was removed at the evaporator
customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-53fb038502ab4f07935ae9aa4f9e55a1
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309735B2

Reaction notes

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