Dichloromethane → (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester

HRID 987308Notes

Reaction equation

HRID 987308 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)[CH3:3].ClCCl.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86595066HCID 86595066, compound

Product 1

HCID 54054668(S)-2-ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl esterYield 32.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (described in Example 41b) (0.45 g; 1.26 mmole), dichloromethane (10 ml), methanesulfonyl chloride (0.216 g; 1.88 mmole) and triethylamine (0.318 g; 3.14 mmole) were mixed at 0° C. and stirred for 3 hours at that temperature and then at room temperature over night. The reaction mixture was poured into ethyl acetate (50 ml). Triethylamine hydrochloride salt was filtered off and the filtrate evaporated. The residue was redissolved and extracted with ethyl acetate and water. The organic phase was washed once more with water, dried with sodium sulfate and evaporated. Chromatography with diethyl ether:petroleum ether (1:3, 1:1, 3:1) as eluant gave 0.18 g (32.8% yield) of (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester.

Workup

  1. waitat room temperature over night
  2. filtrationTriethylamine hydrochloride salt was filtered off
  3. customthe filtrate evaporated
  4. dissolutionThe residue was redissolved
  5. extractionextracted with ethyl acetate and water
  6. washThe organic phase was washed once more with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-fcf16f527b1d4d8b9ccef159bdcf675e
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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