HCID 20640784, compound → HCID 178523863, compound

HRID 1533285Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:59])[C@H:10]([CH2:49][C:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[NH:52][CH:51]=1)[NH:11][C:12](=[O:48])[CH:13]([C:39]1[CH:44]=[CH:43][C:42]2[O:45][CH2:46][O:47][C:41]=2[CH:40]=1)[CH2:14][C:15]1[N:16]=[CH:17][N:18](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O.O>[CH2:1]([O:8][C:9](=[O:59])[C@H:10]([CH2:49][C:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[NH:52][CH:51]=1)[NH:11][C:12](=[O:48])[CH:13]([C:39]1[CH:44]=[CH:43][C:42]2[O:45][CH2:46][O:47][C:41]=2[CH:40]=1)[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of Nα-[3-(1-triphenylmethylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-L-tryptophan benzyl ester (290 mg) in 80% acetic acid-water (5 ml) was stirred at 50° C. for 5 hours. The resulting mixture was cooled to ambient temperature and the solution was diluted with water. Carbinol was removed by filtration and the filtrate was neutralized with saturated sodium hydroxide aqueous solution, and then the aqueous layer was extracted with ethyl acetate. Drying, filtering and removal of the solvents afforded Nα-[3-(imidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-L-tryptophan benzyl ester (180 mg) as a yellow powder.

Workup

temperatureThe resulting mixture was cooled to ambient temperature
customCarbinol was removed by filtration
extractionthe aqueous layer was extracted with ethyl acetate
customDrying
filtrationfiltering
customremoval of the solvents

Sources & evidence

ORD record: ord-81d422feea5b4aebb010a19bc49ebea6
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207686B1

Reaction notes

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