Acetic Anhydride → HCID 66547000, compound

HRID 1746930Notes

Reaction equation

HRID 1746930 reaction equation
[C:1]([C:4]1[O:8][C:7]2[C:9]([O:18][C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:10]3[C:15](=[C:16]([OH:17])[C:6]=2[CH:5]=1)[CH:14]=[CH:13][CH:12]=[CH:11]3)(=[O:3])[CH3:2].[C:30](OC(=O)C)(=[O:32])[CH3:31].C(OCC)(=O)C>CN(C=O)C>[C:1]([C:4]1[O:8][C:7]2[C:9]([O:18][C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:10]3[C:15](=[C:16]([O:17][C:30](=[O:32])[CH3:31])[C:6]=2[CH:5]=1)[CH:14]=[CH:13][CH:12]=[CH:11]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 66546822HCID 66546822, compound

Product 1

HCID 66547000HCID 66547000, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an 100 ml round-bottom flask, 0.8 gram (2.0 mmoles) of 2-acetyl-4-hydroxy-9-[(tert-butoxycarbonyl)amino]acetoxy-naphtho[2,3-b]furan (prepared in example 12) was dissolved in 30 ml of DMF with mild heating. To the solution, added 0.9 ml of TEA and 0.5 ml of acetic anhydride. The mixture was sealed or isolated from air, and then had been stirred vigorously at room temperature overnight. After addition of 100 ml of ethyl acetate, the reaction mixture was extracted with 80 ml of ice-cooled aqueous 3% citric acid solution twice, and dried with anhydrous sodium sulfate. The organic phase was evaporated to dryness. Product was purified by silica gel chromatograph using dichloromethane as elution solvent. 0.6 gram (1.36 mmole) of product was obtained with yield of 68.0% and characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 1.44 (s, 9H), 2.62 (s, 3H), 2.63 (s, 3H), 4.34 (d, J=6, 2H), 7.67-7.71 (m, 3H), 8.15-8.17 (m, 2H), 8.25 (s, 1H). Mass (M+H) is 442, Mass [M-(tert-butyl)+2H] is 386.

Workup

  1. customThe mixture was sealed
  2. customisolated from air
  3. extractionthe reaction mixture was extracted with 80 ml of ice-
  4. temperaturecooled aqueous 3% citric acid solution twice
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe organic phase was evaporated to dryness
  7. customProduct was purified by silica gel chromatograph
  8. washas elution solvent

Sources & evidence

ORD record
ord-152d5d16795e4583ac6666cf5fa09a98
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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