Water → HCID 54390515, compound

HRID 1720815Notes

Reaction equation

HRID 1720815 reaction equation
[C:1]([O:5][C:6](=[O:26])[C@H:7]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O:44][CH:45]([CH2:53][O:54][C:55](=[O:71])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[CH2:46][S:47][CH2:48][CH2:49][C:50](O)=[O:51])(=[O:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[C@H:7]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:50](=[O:51])[CH2:49][CH2:48][S:47][CH2:46][CH:45]([O:44][C:27](=[O:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:53][O:54][C:55](=[O:71])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])=[CH:12][CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 54192013HCID 54192013, compound

Product 1

HCID 54390515HCID 54390515, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24387Phosphorus trichlorideSolvent

Procedure

To a solution of 4-aminobenzoylaspartic acid di-t-butyl ester (168 mg) in pyridine (2.3 ml), phosphorus trichloride (0.02 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 64 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 =3:1) to yield the title compound (197 mg, yield 85%) as a wax-like substance.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 64 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 =3:1)

Sources & evidence

ORD record
ord-4054ca15b33c4e9983a8b14483b48b45
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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