Water → 4-(6,7-bis(palmitoyloxy)-4-thiaheptanoyl)amino-N-(1,3-bis(t-butyloxycarbonyl)propyl)phthalimide

HRID 1720834Notes

Reaction equation

HRID 1720834 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH:11]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6](=[O:7])[C:5]2=[CH:28][CH:29]=1.[C:30]([O:47][CH:48]([CH2:56][O:57][C:58](=[O:74])[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][CH2:72][CH3:73])[CH2:49][S:50][CH2:51][CH2:52][C:53](O)=[O:54])(=[O:46])[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][CH2:44][CH3:45].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:30]([O:47][CH:48]([CH2:56][O:57][C:58](=[O:74])[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][CH2:72][CH3:73])[CH2:49][S:50][CH2:51][CH2:52][C:53]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH:11]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C:6](=[O:7])[C:5]2=[CH:28][CH:29]=1)=[O:54])(=[O:46])[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][CH2:44][CH3:45]

Participants

6

Reactant 3

HCID 962WaterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 224186114-amino-N-(1,3-bis-(t-butyloxycarbonyl)propyl)phthalimide

Product 1

HCID 224185684-(6,7-bis(palmitoyloxy)-4-thiaheptanoyl)amino-N-(1,3-bis(t-butyloxycarbonyl)propyl)phthalimideYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24387Phosphorus trichlorideSolvent

Procedure

To a solution of 4-amino-N-(1,3-bis-(t-butyloxycarbonyl)propyl)phthalimide (178 mg) in pyridine (2.3 ml), phosphorus trichloride (0.020 ml) was added, followed by stirring at room temperature for 2 hours. To this mixture, 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 24 (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:acetone=3:1) to yield the title compound (190 mg, yield 80%) 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:acetone=3:1)

Sources & evidence

ORD record
ord-faeee9dd56c34a11982e19302e6986d4
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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