Water → E-(S)-2-Ethanesulfonylamino-N-{2-[3-methoxy-4-(3-phenyl-allyloxy)-phenyl]-ethyl}-3-methyl-butyramide

HRID 1862493Notes

Reaction equation

HRID 1862493 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:21])[C@@H:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[O:22][CH3:23].Br[CH2:25]/[CH:26]=[CH:27]/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:34][O-].[Na+].O>CO>[CH2:20]([S:17]([NH:16][C@@H:12]([CH:13]([CH3:15])[CH3:14])[C:11]([NH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:25]/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:3]([O:22][CH3:23])[CH:4]=1)=[O:21])(=[O:19])=[O:18])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 5357478Cinnamyl bromideHCID 10882483(S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramideHCID 10942334Sodium Methoxide

Product 1

HCID 59045568E-(S)-2-Ethanesulfonylamino-N-{2-[3-methoxy-4-(3-phenyl-allyloxy)-phenyl]-ethyl}-3-methyl-butyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramide (2.5 g), E-(3-bromo-propenyl)-benzene(1.5 g) and sodium methoxide (9 ml 1M solution in methanol) in methanol (30 ml) is heated to reflux for 4 hours. Upon cooling water (400 ml) is added. The mixture is extracted with ethyl acetate (2×300 ml). The organic layers are washed with brine (100 ml), dried (MgSO4) and evaporated. The resulting residue is purified by recrystallisation (ethyl acetate/hexane). E-(S)-2-Ethanesulfonylamino-N-{2-[3-methoxy-4-(3-phenyl-allyloxy)-phenyl]-ethyl}-3-methyl-butyramide is obtained, m.p. 128-133° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. additionis added
  4. extractionThe mixture is extracted with ethyl acetate (2×300 ml)
  5. washThe organic layers are washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe resulting residue is purified by recrystallisation (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c7f7c3a11105498f9720f59fa4b26530
Source dataset
uspto-grants-2003_03
Patent number
US06538016B2

Reaction notes

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