Dicyclohexylcarbodiimide → N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide

HRID 1980193Notes

Reaction equation

HRID 1980193 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([N:5]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:4].O1CCOCC1.O[N:40]1[C:44](=[O:45])[CH2:43][CH2:42][C:41]1=[O:46].C1(N=C=NC2CCCCC2)CCCCC1>O.CCCCCC>[F:1][C:2]([F:31])([F:32])[C:3]([N:5]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([O:28][N:40]2[C:44](=[O:45])[CH2:43][CH2:42][C:41]2=[O:46])=[O:27])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:4]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 20437350N-trifluoroacetyl-4-(hexadecylamino)benzoic acid

Product 1

HCID 20437360N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a stirred ice-cold solution of 18.3 g. of p-(2,2,2-trifluoro-N-hexadecylacetamido)benzoic acid in 80 ml. of dioxane is added successively 4.84 g. of N-hydroxysuccinimide and 9.16 g. of dicylohexylcarbodiimide. After 18 hours at 0°-5° C. the mixture is stirred vigorously for one hour with hexane and water and filtered. The hexane layer is washed with water, dried over magnesium sulfate, and concentrated to give an oil.

Workup

  1. filtrationfiltered
  2. washThe hexane layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-123a317fa24c47769f939d8663431f36
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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