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

HRID 378333Notes

Reaction equation

HRID 378333 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].[CH2:19]([O:24][C:25](=[O:38])[C@H:26]([CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH2:27])[CH2:20][CH:21]([CH3:23])[CH3:22]>C1(C)C(C)=CC=CC=1>[CH3:23][CH:21]([CH2:20][CH2:19][O:24][C:25]([C:26]1[CH:28]=[C:29]2[C:30](=[C:16]([C:11]3[CH:10]=[CH:9][C:8]4[C:7](=[O:18])[CH:6]=[C:5]([NH:4][C:1]([CH3:2])=[O:3])[C:14](=[O:15])[C:13]=4[N:12]=3)[N:27]=1)[NH:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:37]2=1)=[O:38])[CH3:22]

Participants

4

Reactant 2

HCID 11586798N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamideHCID 11594264L-tryptophan isoamyl ester

Product 1

HCID 98920077-N-acetyldemethyllavendamycin isoamyl esterYield 429%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7-Acetamido-2-formylquinoline-5,8-dione (23) (prepared as described in Example 23) (244 mg, 0.1 mmol), L-tryptophan isoamyl ester (37) (prepared as described in Example 37) (239 mg, 1 mmol) and xylene (64 ml) were mixed. The mixture was stirred and slowly heated in an oil bath from room temperature to 110° C. over a one-hour period, and then from 110° C. to 140° C. over a 3-hr period. The hot reaction mixture was filtered to remove the brown impurity. The filtrate was evaporated under vacuum. The residue was treated with ethyl-acetate/hexane to give an orange solid (213 mg, 42% yield).

Workup

  1. temperatureslowly heated in an oil bath from room temperature to 110° C. over a one-hour period
  2. waitfrom 110° C. to 140° C. over a 3-hr period
  3. filtrationThe hot reaction mixture was filtered
  4. customto remove the brown impurity
  5. customThe filtrate was evaporated under vacuum
  6. additionThe residue was treated with ethyl-acetate/hexane

Sources & evidence

ORD record
ord-ba1a4b5203b54ff29931e2b8a723975d
Source dataset
uspto-grants-2000_02
Patent number
US06030983

Reaction notes

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