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Trifluoroacetic acid → 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionic acid

HRID 1006124
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HRID 1006124 반응식
[CH2:1]1[O:38][C:37]2[CH:36]=[CH:35][C:5]([CH2:6][N:7]([S:22]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([O:32][CH3:33])=[CH:27][C:26]=3[CH3:34])(=[O:24])=[O:23])[C@H:8]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][C:3]=2[O:2]1.FC(F)(F)C(O)=O>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:1]1[O:38][C:37]2[CH:36]=[CH:35][C:5]([CH2:6][N:7]([S:22]([C:25]3[C:26]([CH3:34])=[CH:27][C:28]([O:32][CH3:33])=[CH:29][C:30]=3[CH3:31])(=[O:23])=[O:24])[C@H:8]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=2[O:2]1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 18337582tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate

생성물 1

HCID 183375492(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionic acid수율 99.1%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride
용매

실험 절차

A solution of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate (1.37 g, 2 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 two 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-methanesulfonylamino-propionic acid as a tan green foamy solid (1.02 g).

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-e9e478ebf79248f3adb0dd61188b23be
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06787559B2

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