Water → HCID 54007799, compound

HRID 1720839Notes

Reaction equation

HRID 1720839 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@H:7]([CH2:18][CH2:19][S:20][CH3:21])[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:23]([O:40][CH:41]([CH2:49][O:50][C:51](=[O:67])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:42][S:43][CH2:44][CH2:45][C:46](O)=[O:47])(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].O>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[C@H:7]([CH2:18][CH2:19][S:20][CH3:21])[NH:8][C:9](=[O:17])[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:46](=[O:47])[CH2:45][CH2:44][S:43][CH2:42][CH:41]([O:40][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:49][O:50][C:51](=[O:67])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[CH:14][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 54079996HCID 54079996, compound

Product 1

HCID 54007799HCID 54007799, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-aminobenzoylmethionine t-butyl ester (160 mg) in pyridine (5 ml), phospholic trichloride (0.022 ml) was added, followed by stirring at room temperature for 2 hours. After addition of 6,7-bis(palmitoyloxy)- 4-thiaheptanoic acid (164 mg) as obtained in Reference Example 4, the reaction mixture was stirred 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, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to yield the title compound (163 mg, yield 68%) as a colorless wax-like substance.

Workup

  1. customas obtained in Reference Example 4
  2. stirringthe reaction mixture was stirred 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, 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=3:2)

Sources & evidence

ORD record
ord-cd5e56008b5d49b6a65237cadb11f1a3
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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