Water → HCID 10629927, compound

HRID 1720813Notes

Reaction equation

HRID 1720813 reaction equation
[C:1]([O:5][C:6](=[O:28])[C@H:7]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:29]([O:46][CH:47]([CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[CH2:48][S:49][CH2:50][CH2:51][C:52](O)=[O:53])(=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:28])[C@H:7]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:52](=[O:53])[CH2:51][CH2:50][S:49][CH2:48][CH:47]([O:46][C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])=[CH:14][CH:13]=1)(=[O:10])=[O:11])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 10787946HCID 10787946, compound

Product 1

HCID 10629927HCID 10629927, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24387Phosphorus trichlorideSolvent

Procedure

To a solution of 4-aminobenzenesulfonylglutamic acid di-t-butyl ester (189 mg) in pyridine (2.3 ml), phosphorus trichloride (0.023 ml) was added, followed by stirring at room temperature for 2 hours. To the mixture, 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (150 mg) was added, followed by stirring at room temperature for 24 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to yield the title compound (213 mg, yield 89%) as a wax-like substance.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 24 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with a 5% aqueous solution of citric acid
  5. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d63d66ae46a44b08becd295bd86954c9
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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