Acetylacetone → HCID 57503336, compound

HRID 1669771Notes

Reaction equation

HRID 1669771 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[CH3:15][C:16](=O)[CH2:17][C:18](=[O:20])[CH3:19].[NH2:22]/[C:23](/[CH3:42])=[CH:24]/[C:25]([O:27][C@H:28]1[CH2:32][C:31](=[O:33])[N:30]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]1=[O:41])=[O:26]>CC(O)C>[C:18]([C:17]1[C@@H:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:24]([C:25]([O:27][C@H:28]2[CH2:32][C:31](=[O:33])[N:30]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]2=[O:41])=[O:26])=[C:23]([CH3:42])[NH:22][C:16]=1[CH3:15])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 31261AcetylacetoneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 59158009HCID 59158009, compound

Product 1

HCID 57503336HCID 57503336, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1 g (5.32 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde is introduced into 25 ml of 2-propanol and heated under reflux with 0.93 g (9.3 mmol) of 2,4-pentanedione and 1.53 g (5.32 mmol) of (3S)-1-benzyl-2,5-dioxopyrrolidin-3-yl (2E)-3-aminobut-2-enoate [preparation analogous to D. Alker et al., Eur. J. Med. Chem. 26 (9), 907-913 (1991), starting from (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione] overnight. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 950 mg (33% of theory) of the desired product are obtained as 4R/4S diastereomer mixture.

Workup

  1. temperatureheated
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-362750cbb5c242dc917f007392bdc928
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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