Methyl acetoacetate → HCID 57559686, compound

HRID 1723830Notes

Reaction equation

HRID 1723830 reaction equation
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[CH2:11]([O:13][C:14]1[O:15][C:16](=[O:28])[C:17]2[CH:27]=[C:26]3[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]3)=[CH:20][C:18]=2[N:19]=1)[CH3:12]>C1C=CC=CC=1>[C:5](/[C:4](=[C:16](\[C:17]1[C:18]([NH:19][C:14]([O:13][CH2:11][CH3:12])=[O:15])=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=1)/[OH:28])/[C:3]([O:9][CH3:10])=[O:8])(=[O:6])[CH3:7]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 57559687HCID 57559687, compound

Product 1

HCID 57559686HCID 57559686, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a dispersion of sodium hydride (95%) (1.00 g, 41.7 mmol, 2.1 equiv) in anhydrous benzene (250 ml) under nitrogen was added dropwise methyl acetoacetate (6.5 ml, 7.00 g, 60.3 mmol, 3.1 equiv) and the mixture was stirred at room temp for 1 hour. 2-ethoxy-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-2) (4.72 g, 19.5 mmol, 1.0 equiv) was added and the reaction continued stirring at room temperature for 20 hours. The reaction was quenched with water and the organic layer was separated, and extracted three times with water. The emulsion and combined aqueous layers were made acidic with conc. HCl and stirred for 20 hours. The solid precipitate was filtered and dried to yield methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-2-naphthyl}-3-hydroxyprop-2-enoate (1-3) as a yellow solid. LRMS m/z (M+H) 358.3 found, 358.1 required.

Workup

  1. stirringthe reaction continued stirring at room temperature for 20 hours
  2. customThe reaction was quenched with water
  3. customthe organic layer was separated
  4. extractionextracted three times with water
  5. stirringstirred for 20 hours
  6. filtrationThe solid precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-ba3c416db1ae4836a1deb2b6991e3b4a
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

Loading…