Dichloromethane → 4-[6,7-Bis(octadecylcarbamoyloxy)-4thiaheptanoylamino]benzoylglutamic acid

HRID 1720821Notes

Reaction equation

HRID 1720821 reaction equation
C([O:5][C:6](=[O:79])[C@H:7]([CH2:70][CH2:71][C:72]([O:74]C(C)(C)C)=[O:73])[NH:8][C:9](=[O:69])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:68])[CH2:18][CH2:19][S:20][CH2:21][CH:22]([O:46][C:47](=[O:67])[NH:48][CH2:49][CH2:50][CH2:51][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])[CH2:23][O:24][C:25](=[O:45])[NH:26][CH2:27][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][CH2:42][CH2:43][CH3:44])=[CH:12][CH:11]=1)(C)(C)C.ClCCl>FC(F)(F)C(O)=O>[CH2:49]([NH:48][C:47]([O:46][CH:22]([CH2:23][O:24][C:25](=[O:45])[NH:26][CH2:27][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][CH2:42][CH2:43][CH3:44])[CH2:21][S:20][CH2:19][CH2:18][C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][C@H:7]([C:6]([OH:79])=[O:5])[CH2:70][CH2:71][C:72]([OH:74])=[O:73])=[O:69])=[CH:15][CH:14]=1)=[O:68])=[O:67])[CH2:50][CH2:51][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]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 107487704-[6,7-Bis(octadecylcarbamoyloxy)-4-thiaheptanoylamino]benzoyl-glutamic acid di-t-butyl ester

Product 1

HCID 106298574-[6,7-Bis(octadecylcarbamoyloxy)-4thiaheptanoylamino]benzoylglutamic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[6,7-bis(octadecylcarbamoyloxy)-4-thiaheptanoylamino]benzoyl-glutamic acid di-t-butyl ester as obtained in Example 31 (100 mg) in trifiuoroacetic acid (2 ml)-dichloromethane (0.5 ml) was stirred at room temperature for 1 hour. After solvent concentration under reduced pressure, the resulting residue was crystallized from chloroform-methanolwater to yield the title compound (99 mg, yield 100%) as a colorless powder.

Workup

  1. concentrationAfter solvent concentration under reduced pressure
  2. customthe resulting residue was crystallized from chloroform-methanolwater

Sources & evidence

ORD record
ord-2d01af0cf279447b995f321423b24518
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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