Dicyclohexylcarbodiimide → N-(6-phenylhexyl)-(4-benzylthio-2-oxoazetidin-1-yl)acetamide

HRID 1603648Notes

Reaction equation

HRID 1603648 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C2N=NNC=2C=CC=1.[CH2:39]([S:46][CH:47]1[N:50]([CH2:51][C:52](O)=[O:53])[C:49](=[O:55])[CH2:48]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:52](=[O:53])[CH2:51][N:50]2[CH:47]([S:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:48][C:49]2=[O:55])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1455586-Phenylhexan-1-amineHCID 19605256(4-Benzylthio-2-oxoazetidin-1-yl)acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 19605281N-(6-phenylhexyl)-(4-benzylthio-2-oxoazetidin-1-yl)acetamideYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-phenylhexylamine (Morse M. A. et al., Cancer Research, 1991, 1846), (7.0 g, 40 mmol) in DMF (20 ml) was added to DCC (8.2 g, 40 mmol), hydroxybenzotriazole (5.3 g, 39 mmol) and (4-benzylthio-2-oxoazetidin-1-yl)acetic acid (10 g, 39 mmol) and the mixture stirred for 2 hours at room temperature. Ethyl acetate (250 ml) was added, the precipitate filtered, the filtrate washed with dil NaHCO3, water (×2), dried (MgSO4) and evaporated to an oil which was purified by flash chromatography on silica gel using hexane/ethyl acetate (1:1). Evaporation of the appropriate fractions followed by treatment with hexane gave a white solid (11.2 g, 70%), mp 65-70° C.

Workup

  1. filtrationthe precipitate filtered
  2. washthe filtrate washed with dil NaHCO3, water (×2)
  3. dry with materialdried (MgSO4)
  4. customevaporated to an oil which
  5. customwas purified by flash chromatography on silica gel
  6. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-c9fa6819c6a942b5909480318dede038
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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