Dimethyl Sulfoxide → HCID 22988750, compound

HRID 987283Notes

Reaction equation

HRID 987283 reaction equation
[OH-].[Na+].CS(C)=O.C[O:8][C:9](=[O:22])[CH:10]([S:19][CH2:20][CH3:21])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[C:23]([O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:33][CH:32]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>O.O1CCCC1>[C:23]([O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][O:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH:10]([S:19][CH2:20][CH3:21])[C:9]([OH:8])=[O:22])=[CH:13][CH:14]=2)=[CH:33][CH:32]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium Hydroxide2×HCID 113267772-(4-(Tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonateHCID 54450181Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester

Product 1

HCID 22988750HCID 22988750, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (0.14 g; 3.5 mmole) was pulverized and added to DMSO (15 ml). 2-ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester (described in Example 43b) (0.21 g, 0.87 mmole) was added and the resulting mixture was stirred at room temperature for 10 minutes before addition of 2-(4-(tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.342 g; 0.87 mmole). The reaction mixture was stirred at room temperature for 4 hours. Sodium hydroxide (1.08 g; 2.7 mmole) was dissolved in water (15 ml) and added to the reaction mixture followed by addition of tetrahydrofuran (5 ml). The reaction mixture was stirred at room temperature over night. Most of the solvents were evaporated. The residue was treated with diethyl ether and water and the phases were separated. The organic phase was dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using a gradient system of petroleum ether: diethyl ether (90:10, 75:25, 25;75 and 0:100) gave 0.41 g (34% yield) of 3-[4-{2-(4-[tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid.

Workup

  1. additionadded to the reaction mixture
  2. stirringThe reaction mixture was stirred at room temperature over night
  3. customMost of the solvents were evaporated
  4. additionThe residue was treated with diethyl ether and water
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-1dcc9469efaa4451a983811f7aca606b
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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