Acetic Anhydride → HCID 22707448, compound

HRID 993173Notes

Reaction equation

HRID 993173 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[N:14]1[CH2:19][CH2:18][N:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16][CH2:15]1)([O-])=O.[H][H].C(N(CC)CC)C.[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(O)C.[C].[Pd].CO>[C:45]([NH:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[N:14]1[CH2:19][CH2:18][N:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16][CH2:15]1)(=[O:47])[CH3:46]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22707568HCID 22707568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22707448HCID 22707448, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 464.1 mg (0.99 mmol) of Compound 311 in 15 ml of ethanol was added 100 mg of 10% palladium-carbon, followed by stirring in a stream of hydrogen at room temperature for 4 hours. After the catalyst was separated by filtration using Celite, the solvent was evaporated. The residue was dissolved in 15 ml of dichloromethane, and 0.70 ml (5.02 mmol) of triethylamine and 0.19 ml of acetic anhydride were added thereto, followed by overnight stirring at room temperature. After methanol was added to the reaction mixture, the solvent was evaporated, and the residue was purified by silica gel chromatography to give the desired compound as colorless crystals.

Workup

  1. customAfter the catalyst was separated by filtration
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 15 ml of dichloromethane
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-81956767a6724012b3f72ea7ea15e0aa
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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