Trifluoroacetic acid → HCID 22418615, compound

HRID 1720825Notes

Reaction equation

HRID 1720825 reaction equation
C([O:5][C:6](=[O:58])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:57])[CH2:15][CH2:16][S:17][CH2:18][CH:19]([O:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:20][O:21][C:22](=[O:38])[CH2:23][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][CH3:37])=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[C:40]([O:39][CH:19]([CH2:20][O:21][C:22](=[O:38])[CH2:23][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][CH3:37])[CH2:18][S:17][CH2:16][CH2:15][C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:58])=[O:5])=[CH:8][CH:9]=1)=[O:57])(=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54427159HCID 54427159, compound

Product 1

HCID 22418615HCID 22418615, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylamino]benzoic acid t-butyl ester as obtained in Example 45 (1.05 g) in chloroform (5 ml)-trifiuoroacetic acid (6 ml) was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the residue was crystallized from methanol-water to yield 4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylamino]benzoic acid (992 mg, yield 100%) as a colorless crystal. A solution of 4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylamino]benzoic acid as obtained above (200 mg), 7-t-butyl ester-glutamyl-glutamic acid di-t-butyl ester as obtained in Reference Example 26 (126 mg), DEPC (63 mg) and triethylamine (78 mg) in dimethylformarnide (6 ml) was stirred at room temperature for 30 minutes. The solvent was concentrated; the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate:chloroform=2:1) to yield the title compound (210 mg, yield 68%) as a colorless amorphous substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was crystallized from methanol-water

Sources & evidence

ORD record
ord-363df3e695c645e0ac080c7f61facc6e
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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