Potassium Carbonate → Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate

HRID 1375723Notes

Reaction equation

HRID 1375723 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1)(=O)=O.[CH2:23]([O:25][C:26](=[O:39])[C@@H:27]([O:36][CH2:37][CH3:38])[CH2:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:19]([O:18][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][O:5][C:32]2[CH:31]=[CH:30][C:29]([CH2:28][C@H:27]([O:36][CH2:37][CH3:38])[C:26]([O:25][CH2:23][CH3:24])=[O:39])=[CH:34][CH:33]=2)=[CH:10][CH:11]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 219936273-{4-[(Tert-butoxycarbonyl)amino]phenyl}propyl methanesulfonate

Product 1

HCID 86613339Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoateYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propyl methanesulfonate (360 mg, 1.093 mmol) and (S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (260 mg, 1.093 mmol) were mixed in acetonitrile (30 ml). Potassium carbonate (anhydrous, 226.6 mg 1.639 mmol) was added. The mixture was heated to reflux overnight and thereafter it was evaporated to dry. Ethyl acetate (20 ml) and water (5 ml) were added into the residue. The two phases were separated and the water phase was extracted with ethyl acetate (10 ml×2). The organic phases were combined and washed with 0.1 M sodium hydroxide aqueous solution, water and brine and dried with magnesium sulfate. The solvent was evaporated in vacuum and an oil mixture was left. Column chromatography of the oil mixture on silica gel using ethyl acetate/heptane (20:80) as eluant gave the desired product (389 mg), yield 75.5%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customit was evaporated
  4. customto dry
  5. additionEthyl acetate (20 ml) and water (5 ml) were added into the residue
  6. customThe two phases were separated
  7. extractionthe water phase was extracted with ethyl acetate (10 ml×2)
  8. washwashed with 0.1 M sodium hydroxide aqueous solution, water and brine
  9. dry with materialdried with magnesium sulfate
  10. customThe solvent was evaporated in vacuum
  11. waitan oil mixture was left

Sources & evidence

ORD record
ord-6e3a5db504a44cc1b453b1905b3b7e00
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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