Ethylene carbonate → HCID 68861986, compound

HRID 2109417Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[OH:32])[C:6]([NH:8][NH:9][C:10]([C:12]1[O:13][CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])=[O:7])#[N:2].C1(=O)O[CH2:36][CH2:35][O:34]1>[I-].C([N+](CC)(CC)CC)C.CN(C=O)C>[OH:34][CH2:35][CH2:36][O:32][C:31]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][NH:9][C:10]([C:12]2[O:13][CH:14]=[C:15]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:11])=[O:7])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the compound of Example 18 (0.42 g), ethylene carbonate (0.088 g), tetraethylammonium iodide (0.026 g) and DMF (10 ml) was stirred at 100° C. for 2 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: 50%→90% ethyl acetate/hexane gradient), thereby giving 0.26 g of the desired compound. HPLC retention time: 6.31 minutes.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: 50%→90% ethyl acetate/hexane gradient)

Sources & evidence

ORD record: ord-667f420deb374edb877333de6ace7c89
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514452B2

Reaction notes

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