Potassium Carbonate → 3-{4-[2-(4-Tert-butoxycarbonylaminophenyl)ethoxy]-3-methoxyphenyl}-2-ethoxypropanoic acid ethyl ester

HRID 987294Notes

Reaction equation

HRID 987294 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](OCC2C=CC=CC=2)=[C:9]([O:21][CH3:22])[CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:33]([O:37][C:38]([NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][O:49]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:43][CH:42]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>C(#N)C>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:49][CH2:48][CH2:47][C:44]2[CH:43]=[CH:42][C:41]([NH:40][C:38]([O:37][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:39])=[CH:46][CH:45]=2)=[C:9]([O:21][CH3:22])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113267772-(4-(Tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonateHCID 541620193-(4-Benzyloxy-3-methoxyphenyl)-2-ethoxypropanoic acid ethyl ester

Product 1

HCID 573178123-{4-[2-(4-Tert-butoxycarbonylaminophenyl)ethoxy]-3-methoxyphenyl}-2-ethoxypropanoic acid ethyl esterYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(4-Benzyloxy-3-methoxyphenyl)-2-ethoxypropanoic acid ethyl ester (0.5 g; 1.86 mmole) was dissolved in acetonitrile and potassium carbonate (0.53 g; 3.91 mmole) was added. 2-[4-(tert-Butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.755 g, 1.92 mmole) was added. The resulting mixture was stirred and refluxed over night then filtered and the filtrate was evaporated. The residue was treated with sodium hydroxide (0.5 M) and diethyl ether. The phases were separated and the organic phase was dried with magnesium sulfate. Evaporation gave 0.7 g (77.2% yield) of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]-3-methoxyphenyl}-2-ethoxypropanoic acid ethyl ester.

Workup

  1. temperaturerefluxed over night
  2. filtrationthen filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was treated with sodium hydroxide (0.5 M) and diethyl ether
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried with magnesium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-ff73e03b767641c58c06109f2807a982
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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