N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide → 7-N-acetyldemethyllavendamycin methyl ester

HRID 1278588Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([CH:16]=O)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)(=[O:3])[CH3:2].CN(C[CH2:23][O:24][C:25](=[O:39])[C@H:26]([CH:28](C)[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH2:27])C>C1(OC)C=CC=CC=1>[CH3:2][C:1]([NH:4][C:5]1[C:14](=[O:15])[C:13]2[N:12]=[C:11]([C:16]3[N:27]=[C:26]([C:25]([O:24][CH3:23])=[O:39])[CH:28]=[C:29]4[C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[NH:31][C:30]=34)[CH:10]=[CH:9][C:8]=2[C:7](=[O:18])[CH:6]=1)=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

7-N-ACETYLLAVENDAMYCIN N,N-DIMETHYLAMINOETHYL ESTER (Compound 19, Table I): 7-Acetamido-2-formylquinoline-5,8-dione (23) (prepared as described in Example 23) (317 mg, 0.13 mmol) was dissolved in 16 ml of dry anisole and heated to 80° C. b-methyltryptophan N,N-dimethylaminoethyl ester (41) (prepared as described in Example 41) (37.5 mg, 0.13 mmol) was added with stirring, and the stirred mixture was heated at 100° C. for 5.5 hr. The reaction mixture was allowed to cool to room temperature and the solid was filtered. The filtrate was distilled under vacuum to dryness. Ethyl acetate (3 ml) was added, and the mixture was stirred. Upon filtration 24.5 mg (a yield of 36%) of an orange solid was obtained.

Workup

additionwas added
temperatureto cool to room temperature
filtrationthe solid was filtered
distillationThe filtrate was distilled under vacuum to dryness
additionEthyl acetate (3 ml) was added
stirringthe mixture was stirred
filtrationUpon filtration 24.5 mg (a yield of 36%) of an orange solid
customwas obtained

Sources & evidence

ORD record: ord-5e300ffaddd84793b62fdee589833880
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444684B1

Reaction notes

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