Water → 3-[4-{2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid ethyl ester

HRID 987311Notes

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].C(N(CC)CC)C.[C:35]1([CH2:41][S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>ClCCl>[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:42]([CH2:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:44])=[O:43])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (described in Example 41b) (0.5 g; 1.27 mmole) was dissolved in dichloromethane (10 ml) and triethylamine (0.39 ml; 2.8 mmole) was added. The mixture was cooled to 0° C., Phenylmethanesulphonyl chloride (0.32 g; 1.68 mmole) was added. The reaction mixture was then stirred overnight and the temperature was allowed to reach room temperature. Water was added and the phases were separated. The organic phase was washed with water, dried with magnesium sulfate and evaporated. Chromatography of the residue on silica gel using ethyl acetate/heptane as eluant gave 0.245 g (38% yield) of 3-[4-{2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid ethyl ester.

Workup

customto reach room temperature
customthe phases were separated
washThe organic phase was washed with water
dry with materialdried with magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-d3572cac82cc47ec868041cd4c16ce83
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630600B1

Reaction notes

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