Acetyl chloride → HCID 54080686, compound

HRID 1934672Notes

Reaction equation

HRID 1934672 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:6][NH:7][C:8](=[O:23])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@H:19]([CH3:22])[CH2:20][OH:21].C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>CN(C)C1C=CN=CC=1.ClCCl>[C:36]([O:21][CH2:20][C@H:19]([NH:18][C:10]1[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][C:5]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:23])[CH3:22])(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9821702(R)-Xanthoanthrafil

Product 1

HCID 54080686HCID 54080686, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)-5-nitrobenzamide (5.00 g), 4-dimethylaminopyridine (1.57 g, 12.8 mmol) and triethylamine (1.79 mL) in dichloromethane (150 mL) was added acetyl chloride (1.83 mL), and the mixture was stirred for 5 hours at ambient temperature. The mixture was washed with 1N-hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether. The obtained product was recrystallized from a mixture of ethyl acetate and hexane (1:1) to give (R)-2-(2-acetoxy-1-methylethylamino)-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide as yellow crystals (5.10 g).

Workup

  1. washThe mixture was washed with 1N-hydrochloric acid, water
  2. dry with materialThen, the resultant was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether
  5. customThe obtained product was recrystallized from a mixture of ethyl acetate and hexane (1:1)

Sources & evidence

ORD record
ord-9680632e1909453c91eb1a6ce72de5f2
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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