Ethanol → Dicyclohexylamine

HRID 544497Notes

Reaction equation

HRID 544497 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[S:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[CH3:15][C:16](=[CH2:27])[C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18].[CH2:28](O)C>>[CH:26]1([NH:19][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:9][CH2:10]2)[CH2:28][CH2:21][CH2:20][CH2:24][CH2:25]1.[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([S:7][CH2:15][C@@H:16]([CH3:27])[C:17]([N:19]2[CH2:26][CH2:25][CH2:24][C@H:20]2[C:21]([OH:23])=[O:22])=[O:18])=[O:8])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 132083491-(2-Methylacryloyl)-L-prolineHCID 178514757HCID 178514757, compound

Product 2

HCID 7582DicyclohexylamineHCID 12893586HCID 12893586, compound

Procedure

5 g of 4-chloro-3-sulfamoyl-thiobenzoic acid is added slowly to a stirred solution of 3.6 g of 1-(2-methyl-2-propenoyl)-L-proline in 50 ml of ethanol at room temperature. The resulting mixture is stirred overnight and then concentrated under reduced pressure. To the residue are added ethyl acetate and water. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is treated in an analogous manner of Example 4 to give dicyclohexylamine salt of 1-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-L-proline as white crystalline powder, melting at 143°-146° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue are added ethyl acetate and water
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue is treated in an analogous manner of Example 4

Sources & evidence

ORD record
ord-b3e3ffa3dd65435ba69b78383ce4d5b4
Source dataset
uspto-grants-1984_05
Patent number
US04450275

Reaction notes

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