Water → 3-(3-Chloropropylsulfonylamino)-2-(3-methylureido)-1-octadecylcarbamoyloxypropane

HRID 846988Notes

Reaction equation

HRID 846988 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10](OC(=O)NC)[CH2:11][O:12][C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:7])=[O:6].[CH3:39][N:40]=[C:41]=[O:42].O.C[N:45](C)C=O>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([NH:45][C:41]([NH:40][CH3:39])=[O:42])[CH2:11][O:12][C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:6])=[O:7]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 12228Methyl IsocyanateHCID 148350393-(3-Chloropropylsulfonylamino)-2-methylcarbamoyloxy-1-octadecylcarbamoyloxypropane

Product 1

HCID 148350463-(3-Chloropropylsulfonylamino)-2-(3-methylureido)-1-octadecylcarbamoyloxypropaneYield 88%

Procedure

To a solution of 480 mg of the amine III e1' in 5 ml of N,N-dimethylformamide is added 0.2 ml of methylisocyanate. The mixture is stirred at room temperature for 1 h, poured to water and extracted with ethyl acetate. The extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is subjected to flash chromatography on silica gel in chloroform:methanol (9:1) and recrystallized from ethyl acetate to give 469 mg (88.0% yield) of the titled compound. mp. 87°-90° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-20d748e1ba4846be9a348007784b0419
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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