p-Toluenesulfonic acid → 2,3,4,5,6-Pentahydroxyhexyl 4-(n-hexadecylamino)benzoate

HRID 1439298Notes

Reaction equation

HRID 1439298 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:27](O)[C@H:28]([C@H:30]([C@@H:32]([C@@H:34]([CH2:36][OH:37])[OH:35])[OH:33])[OH:31])[OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:27][CH:28]([OH:29])[CH:30]([OH:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH2:36][OH:37])=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6251MannitolHCID 472634-(Hexadecylamino)benzoic acid

Product 1

HCID 213269562,3,4,5,6-Pentahydroxyhexyl 4-(n-hexadecylamino)benzoate

Procedure

In the manner described in Example 7, 3.62 g. of 4-(n-hexadecylamino)benzoic acid, 1.82 g. of mannitol, and 2.06 g. of p-toluene sulfonic acid are reacted to yield a mixture of mono- and bis-acylated products. Pure 2,3,4,5,6-pentahydroxyhexyl 4-(n-hexadecylamino)benzoate is separated from the mixture by adsorption chromatography using silica gel as the adsorbant.

Workup

  1. customto yield
  2. additiona mixture of mono- and bis-acylated products
  3. customPure 2,3,4,5,6-pentahydroxyhexyl 4-(n-hexadecylamino)benzoate is separated from the mixture by adsorption chromatography

Sources & evidence

ORD record
ord-588f20427c9b46ae96433d4e4d5ce106
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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