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Water → (4-(6,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoyl)amino-benzoyl)glutamic acid di-t-butyl ester

HRID 1720836
Notes
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Reaction equation

HRID 1720836 reaction equation
[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O: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:28]([O:45][CH:46]([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])[CH2:47][S:48][CH2:49][CH:50]([CH3:54])[C:51](O)=[O:52])(=[O:44])[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][CH2:42][CH3:43].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:51](=[O:52])[CH:50]([CH3:54])[CH2:49][S:48][CH2:47][CH:46]([O:45][C:28](=[O:44])[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][CH2:42][CH3:43])[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:12][CH:11]=1)([CH3:3])([CH3:4])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 105324766,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acidHCID 10691066L-Glutamic acid, N-(4-aminobenzoyl)-, bis(1,1-dimethylethyl) ester

Product 1

HCID 10701254(4-(6,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoyl)amino-benzoyl)glutamic acid di-t-butyl esterYield 62%

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
HCID 24387Phosphorus trichlorideSolvent

Procedure

To a solution of 4-aminobenzoylglutamic acid di-t-butyl ester (378 mg) in pyridine (5 ml), phosphorus trichloride (0.044 ml) was added, followed by stirring at room temperature for 2 hours. To this solution, 6,7-bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acid as obtained in Reference Example 42 (336 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 (315 mg, yield 62%) 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-e8e5ecff5b0c448c8aa628bf484d181f
Source dataset
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05506267

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes