Acetyl chloride → HCID 69710047, compound

HRID 2121902Notes

Reaction equation

HRID 2121902 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C@H:7]1[CH2:30][O:29][C:10]2=[CH:11][CH:12]=[C:13]3[C:17]([N:16]([CH2:18][C@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[N:15]=[CH:14]3)=[C:9]2[CH2:8]1)=[N+]=[N-].C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39].C(=O)(O)[O-].[Na+]>CO.[Pd]>[C:25]([Si:22]([CH3:24])([CH3:23])[O:21][C@H:19]([CH3:20])[CH2:18][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]3[O:29][CH2:30][C@H:7]([O:6][CH2:5][CH2:4][NH:1][C:38](=[O:40])[CH3:39])[CH2:8][C:9]3=2)[CH:14]=[N:15]1)([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 91017075HCID 91017075, compound

Product 1

HCID 69710047HCID 69710047, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from step B (0.73 g, 1.69 mmol) and palladium-on-carbon (10%, 0.07 g) in methanol (50 mL) was placed under an atmosphere of hydrogen and stirred overnight. The mixture was filtered, evaporated to an oil (0.61 g, 88%) which was dissolved in dichloromethane (30 mL). To this solution was added triethylamine (0.304 g, 3.01 mmol) and acetyl chloride (0.142 g, 0.129 mL, 1.81 mmol), and the mixture was stirred for 1 h, mixed with a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate. The dried extracts were evaporated to a residue which was purified by chromatography (silica, gradient, 30% to 90% ethyl acetate in hexane) to give an oil (0.41 g, 61%): LCMS (+ESI) m/z 448 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to an oil (0.61 g, 88%) which
  3. dissolutionwas dissolved in dichloromethane (30 mL)
  4. stirringthe mixture was stirred for 1 h
  5. extractionextracted with ethyl acetate
  6. customThe dried extracts were evaporated to a residue which
  7. customwas purified by chromatography (silica, gradient, 30% to 90% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-82fedb4eb3b14de1aabaf7390232dcac
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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