Potassium Carbonate → 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester

HRID 987276Notes

Reaction equation

HRID 987276 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]CS([O-])(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:24][C:25](=[O:38])[C@@H:26]([O:35][CH2:36][CH3:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OC(NC1C=CC(CCCS([O-])(=O)=O)=CC=1)=O)(C)(C)C>[CH2:22]([O:24][C:25](=[O:38])[C@@H:26]([O:35][CH2:36][CH3:37])[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:14][CH:13]=2)=[CH:32][CH:33]=1)[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 229887672-[4-(tert-Butoxycarbonylamino)phenyl]ethylmethanesulfonate

Product 1

HCID 118125123-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl esterYield 99,648.797%

Reagents, catalysts & solvents 2

HCID 229887672-[4-(tert-Butoxycarbonylamino)phenyl]ethylmethanesulfonateCatalystHCID 6342AcetonitrileSolvent

Procedure

2-[4-(tert-Butoxycarbonylamino)phenyl]ethylmethanesulfonate (described in Example40a) (52.9 g; 0.168 mmole), (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (described in Example 40h) (40 g; 0.168 mmole) and potassium carbonate (69.5 g; 0.503 mmole) were mixed in acetonitrile (1200 ml) and refluxed over night. Another portion of 2-[4-(tert-butoxycarbonylamino)phenyl]ethylmethanesulfonate (2.5 g; 7.9 mmole) was added. The reaction mixture was refluxed for 8 more hours then filtered. Evaporation of the filtrate gave 76.6 g 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester.

Workup

  1. temperaturerefluxed over night
  2. temperatureThe reaction mixture was refluxed for 8 more hours
  3. filtrationthen filtered
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-10f591e023e441fb812bbb47e4ea1d63
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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