Dicyclohexylcarbodiimide → Ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)phenyl]carbonylamino}propionate

HRID 859937

Reaction equation

HRID 859937 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:19]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)([CH3:21])[CH3:20].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH2:8][CH:2]([NH:1][C:27]([C:26]2[CH:30]=[CH:31][C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[CH:24][CH:25]=2)=[O:28])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 729724-Isopropoxybenzoic acidHCID 420232Ethyl 2-amino-3-(3,4-dimethoxyphenyl)propanoateHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68826043Ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)phenyl]carbonylamino}propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-amino-3-(3,4-dimethoxyphenyl)propionate (the compound obtained in Example 1-(1)) (15.2 g), 4-isopropyloxybenzoic acid (10.8 g), and 1-hydroxybenzotriazole monohydrate (9.2 g) are dissolved in methylene chloride (120 ml), and thereto is added 1,3-dicyclohexylcarbodiimide (12.4 g) under ice-cooling, and the mixture is stirred at room temperature overnight. The insoluble materials are removed by filtration, and the filtrate is washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals are collected by filtration with diethyl ether to give ethyl 3-(3,4-dimethoxyphenyl)-2-{[4-(isopropyloxy)phenyl]carbonylamino}propionate (24.2 g).

Workup

  1. temperaturecooling
  2. customThe insoluble materials are removed by filtration
  3. washthe filtrate is washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe precipitated crystals are collected by filtration with diethyl ether

Sources & evidence

ORD record
ord-9984419922774c7a9c60caced24db6ca
Source dataset
uspto-grants-2006_12
Patent number
US07153859B2

Linked notes

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