Dicyclohexylcarbodiimide → N-[2-[4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl]ethyl]-3-[2-[2-phenylethoxy]ethylsulphonyl]propanamide

HRID 963566Notes

Reaction equation

HRID 963566 reaction equation
O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Br.[NH2:28][CH2:29][CH2:30][C:31]1[C:39]2[S:38][C:37](=[O:40])[NH:36][C:35]=2[C:34]([OH:41])=[CH:33][CH:32]=1.[C:42]1([CH2:48][CH2:49][O:50][CH2:51][CH2:52][S:53]([CH2:56][CH2:57][C:58](O)=[O:59])(=[O:55])=[O:54])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C.C(O)(=O)C.C(N(CC)CC)C>[OH:41][C:34]1[C:35]2[NH:36][C:37](=[O:40])[S:38][C:39]=2[C:31]([CH2:30][CH2:29][NH:28][C:58](=[O:59])[CH2:57][CH2:56][S:53]([CH2:52][CH2:51][O:50][CH2:49][CH2:48][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)(=[O:54])=[O:55])=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 138142707-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromideHCID 190821643-[2-[2-Phenylethoxy]ethylsulphonyl]propanoic acid

Product 1

HCID 19082162N-[2-[4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl]ethyl]-3-[2-[2-phenylethoxy]ethylsulphonyl]propanamideYield 71%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (0.70 ml), 1-hydroxybenzotriazole hydrate (0.98 g) and finally dicyclohexylcarbodiimide (1.49 g) were added to a stirred solution of 7-[2-aminoethyl]-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide (1.62 g) and the material from step b) (1.75 g) in DMF (25 ml). The whole was stirred for 16 hours at room temperature. Glacial acetic acid (0.1 ml) was added and stirring continued for 15 min. The DMF was removed under reduced pressure and the residue slurried with ethyl acetate (50 ml). The suspended dicyclohexylurea was removed by filtration. The filtrate was washed with saturated aqueous sodium bicarbonate and dried (MgSO4). The solvent was removed under reduced pressure to yield a residue which was purified by column chromatography over silica using 95:5 dichloromethane:ethanol to give the subtitled compound (1.89 g, 71%).

Workup

  1. stirringstirring
  2. waitcontinued for 15 min
  3. customThe DMF was removed under reduced pressure
  4. customThe suspended dicyclohexylurea was removed by filtration
  5. washThe filtrate was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customto yield a residue which
  9. customwas purified by column chromatography over silica using 95:5 dichloromethane

Sources & evidence

ORD record
ord-51c642609de0490a96358d6618093f49
Source dataset
uspto-grants-1998_06
Patent number
US05763465

Reaction notes

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