Trifluoroacetic acid → 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acid

HRID 2298007노트

반응식

HRID 2298007 반응식
C([O:5][C:6](=[O:47])[C@H:7]([N:23]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]2[O:44][CH2:45][O:46][C:40]=2[CH:39]=1)[S:24]([C:27]1[C:32]([CH3:33])=[CH:31][C:30]([O:34][CH3:35])=[CH:29][C:28]=1[CH3:36])(=[O:26])=[O:25])[CH2:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:45]1[O:44][C:41]2[CH:42]=[CH:43][C:38]([CH2:37][N:23]([S:24]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([O:34][CH3:35])=[CH:29][C:28]=3[CH3:36])(=[O:25])=[O:26])[C@H:7]([CH2:8][NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22]3)=[O:11])[C:6]([OH:47])=[O:5])=[CH:39][C:40]=2[O:46]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 69762802tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

생성물 1

HCID 183375482(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acid수율 113.8%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A solution of tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate (915 mg, 1.3 mmol) in 20% trifluoracetic acid-methylene chloride (15 ml) was stirred for 1 hour. Extra trifluoroacetic acid (0.5 ml) was added and stirring continued for 1.5 hours. The material was then condensed on the rotary evaporator and the residue was taken up in toluene (40 ml) and again condensed. This procedure was repeated twice (2×40 ml toluene, to remove traces of trifluoracetic acid) to provide 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionic acid as a golden tan solid (896 mg).

후처리

  1. customcondensed
  2. customon the rotary evaporator
  3. customagain condensed
  4. custom(2×40 ml toluene, to remove traces of trifluoracetic acid)

출처 및 근거

ORD 기록
ord-aaf43d247faa49fe8870a29042204002
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492394B1

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