Water → HCID 67148228, compound

HRID 910315Notes

Reaction equation

HRID 910315 reaction equation
C(OC([CH2:8][NH:9][CH2:10][C:11]1[S:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C@H:23]([O:28][CH2:29][CH3:30])[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)[CH:12]=1)=O)(C)(C)C.O>ClCCl.FC(F)(F)C(O)=O>[CH2:29]([O:28][C@@H:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:12]=[C:11]([CH2:10][NH:9][CH3:8])[S:15][CH:14]=2)=[CH:17][CH:18]=1)[C:24]([O:26][CH3:27])=[O:25])[CH3:30]

Participants

5

Reactant 2

HCID 962WaterHCID 67148287HCID 67148287, compound

Product 1

HCID 67148228HCID 67148228, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5 g (11.5 mmol) of methyl 3-(4-{5-[(tert-butoxycarbonylmethylamino)methyl]thiophen-3-yl}phenyl)-2(S)-ethoxypropanoate are placed in 80 ml of dichloromethane and 4.4 ml of trifluoroacetic acid. After stirring at room temperature for 24 hours, water is added and the reaction medium is extracted with dichloromethane. The dichloromethane phase is washed with aqueous 30% sodium hydroxide solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 50/50 heptane/ethyl acetate mixture. 3.2 g (84%) of methyl 2(S)-ethoxy-3-[4-(5-methylaminomethylthiophen-3-yl)phenyl]propanoate are obtained.

Workup

  1. extractionthe reaction medium is extracted with dichloromethane
  2. washThe dichloromethane phase is washed with aqueous 30% sodium hydroxide solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by thin-layer chromatography on silica
  8. washeluted with a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-8bbeddbce92241b5bb87d4b89035df24
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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