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

HRID 1603663Notes

Reaction equation

HRID 1603663 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.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([S:47][CH:48]2[N:51]([CH2:52][C:53](O)=[O:54])[C:50](=[O:56])[CH2:49]2)=[CH:43][CH:42]=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:53](=[O:54])[CH2:52][N:51]2[CH:48]([S:47][C:44]3[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=3)[CH2:49][C:50]2=[O:56])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1455586-Phenylhexan-1-amineHCID 19605269(4-(4-Methoxyphenylthio)-2-oxoazetidin-1-yl)acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 19605381N-(6-phenylhexyl)-(4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl)acetamideYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-phenylhexylamine (Morse M. A. et al., Cancer Research, 1991, 1846), (1.4 g, 8 mmol) in DMF (50 ml) was added to DCC (1.6 g, 8 mmol), hydroxybenzotriazole (1.0 g, 8 mmol) and (4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl)acetic acid (2.1 g, 8 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 (x2), dried (MgSO4) and evaporated to an oil which was purified by flash chromatography on silica gel using hexane/ethyl acetate (1:3). Evaporation of the appropriate fractions gave the product as a colourless oil, 77% yield. 1H NMR δ (CDCl3) 1.34-1.47 (10H, m, (CH2)5), 2.59 (2H, t, J=7.7 Hz, CH2), 2.83 (1H, dd, J=2.2, 15 Hz, H3a), 3.18-3.36 (3H, m, CH2H3b), 3.78 (3H, s, OCH3), 3.80, 3.99 (each 1H, d, J=15 Hz, NCH2), 4.95 (1H, m, H4), 6.23 (1H, bt, NH), 6.87 (2H, d, J=6.8 Hz, 2, 6 Ph--H), 7.14-7.39 (7H, m, 3, 5 Ph--H, Ph--H).

Workup

  1. filtrationthe precipitate filtered
  2. washthe filtrate washed with dil NaHCO3, water (x2)
  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-c8fe8b2d11b94332a8c3361cbcd6d054
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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