1,1'-Carbonyldiimidazole → 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide

HRID 1666311Notes

Reaction equation

HRID 1666311 reaction equation
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:33]([O:36][C:37]1[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:38]=1[CH2:39][NH:40][CH3:41])([CH3:35])[CH3:34]>ClCCl>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]([N:40]([CH3:41])[CH2:39][C:38]2[CH:42]=[CH:43][CH:44]=[C:45]([O:46][CH3:47])[C:37]=2[O:36][CH:33]([CH3:34])[CH3:35])=[O:8])[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 433884002-Isopropoxy-3-methoxy-benzyl-methylamineHCID 67081678alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid

Product 1

HCID 670818692-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of α-acetoxy-3,4,5-trimethoxyphenyl-acetic acid (5.0 g) in dichloromethane (40 ml) was reacted with 1,1′-carbonyldiimidazole (2.92 g) at room temperature for 30 minutes. The solution was refluxed for 30 minutes, after which 2-isopropoxy-3-methoxy-N-methylbenzylamine (3.26 g) dissolved in dichloromethane (10 ml) was added. The mixture was stirred at room temperature for 2 hours, after which it was washed with aqueous hydrochloric acid (20 ml, is 1M) followed by aqueous sodium hydrogen carbonate (20 ml, 0.5 M). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide (7.27 g).

Workup

  1. temperatureThe solution was refluxed for 30 minutes
  2. additionwas added
  3. washafter which it was washed with aqueous hydrochloric acid (20 ml, is 1M)
  4. customThe organic phase was dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2f81bc0b02fb4639ae46d714207c3d6e
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

Loading…