Phosphorus trichloride → 4-[6,7-Bis(octadecylcarbamoyloxy)-4-thiaheptanoylamino]benzoyl-glutamic acid di-t-butyl ester

HRID 1720820Notes

Reaction equation

HRID 1720820 reaction equation
P(Cl)(Cl)Cl.[C:5]([O:9][C:10](=[O:31])[C@H:11]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)([CH3:8])([CH3:7])[CH3:6].[CH2:32]([NH:50][C:51]([O:53][CH:54]([CH2:62][O:63][C:64](=[O:84])[NH:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[CH2:55][S:56][CH2:57][CH2:58][C:59](O)=[O:60])=[O:52])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>N1C=CC=CC=1>[C:5]([O:9][C:10](=[O:31])[C@H:11]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:59](=[O:60])[CH2:58][CH2:57][S:56][CH2:55][CH:54]([O:53][C:51](=[O:52])[NH:50][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][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:62][O:63][C:64](=[O:84])[NH:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])=[CH:16][CH:15]=1)([CH3:7])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 10691066L-Glutamic acid, N-(4-aminobenzoyl)-, bis(1,1-dimethylethyl) esterHCID 224186236,7-Bis(octadecylcarbamoyloxy)-4-thiaheptanoic acid

Product 1

HCID 107487704-[6,7-Bis(octadecylcarbamoyloxy)-4-thiaheptanoylamino]benzoyl-glutamic acid di-t-butyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of phosphorus trichloride (19 mg) in pyridine (4 ml), 4-aminobenzoyl-glutamic acid di-t-butyl ester (106 mg) was added, followed by stirring at room temperature for 1 hour. To this mixture, 6,7-bis(octadecylcarbamoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 10 (216 mg) was added, followed by stirring at 50° C. for 1 hour. After solvent concentration under reduced pressure, the resulting residue was purified by silica gel preparative TLC (dichloromethane:methanol=50:1×3) to yield the title compound (102 mg, yield 32%) as a colorless solid.

Workup

  1. additionwas added
  2. stirringby stirring at 50° C. for 1 hour
  3. concentrationAfter solvent concentration under reduced pressure
  4. customthe resulting residue was purified by silica gel preparative TLC (dichloromethane:methanol=50:1×3)

Sources & evidence

ORD record
ord-980f4e385ea54890b348d307e97eb936
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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