Sodium Hydroxide → 3-[4-{2-(4-[Tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid methyl ester

HRID 987282Notes

Reaction equation

HRID 987282 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5](=[O:18])[CH:6]([S:15][CH2:16][CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[C:19]([O:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:29][CH:28]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CS(C)=O>[CH3:3][O:4][C:5](=[O:18])[CH:6]([S:15][CH2:16][CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:34][CH2:33][C:30]2[CH:29]=[CH:28][C:27]([NH:26][C:24]([O:23][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:25])=[CH:32][CH:31]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 113267772-(4-(Tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonateHCID 54450181Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester

Product 1

HCID 544208783-[4-{2-(4-[Tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid methyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydroxide (0.045 g; 1.25 mmole) was pulverized and added to DMSO (10 ml). 2-Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.21 g; 0.87 mmole) was added followed by addition of 2-[4-(tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.342; 0.87 mmole). The reaction mixture was stirred at room temperature for 3 hours then all the starting material were consumed according to LC-MS. Water (10 ml) and tetrahydrofuran (5 ml) were added and the stirring was continued over night. Then the reaction mixture was treated with diethyl ether and water and in order to avoid foam formation diluted hydrochloric acid was added. The phases were separated and the organic phase was washed three times with water. The water phases were combined and washed once again with diethyl ether. All the organic phases were combined, dried with sodium sulfate and evaporated. Chromatography in ether:petroleum ether (1:9 and 1:3) gave 0.18 g (41.4% yield) of 3-[4-{2-(4-[tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid methyl ester.

Workup

  1. customall the starting material were consumed
  2. additionWater (10 ml) and tetrahydrofuran (5 ml) were added
  3. waitthe stirring was continued over night
  4. additionThen the reaction mixture was treated with diethyl ether and water and in order
  5. additionwas added
  6. customThe phases were separated
  7. washthe organic phase was washed three times with water
  8. washwashed once again with diethyl ether
  9. dry with materialdried with sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-a4f14261e93d4417a7a337f17fc9ee7d
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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