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Hydrochloric Acid → trans-4-[(3-Indolylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylic acid

HRID 1034246
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HRID 1034246 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:13][C@H:14]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C@H:15]2[C:26]([O:28]CC)=[O:27])=[O:12])=[CH:2]1.C1COCC1.CCO.[OH-].[Li+].Cl>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:13][C@@H:14]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C@H:15]2[C:26]([OH:28])=[O:27])=[O:12])=[CH:2]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 67794878Ethyl cis-4-[(1H-indol-3-ylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

생성물 1

HCID 67794351trans-4-[(3-Indolylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylic acid수율 25.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To the title compound of example 8 (520 mg, 1.28 mmol) in 1:4 THF/EtOH (20 ml) was added lithium hydroxide (46 mg (1.92 mmol) in H2O (10 ml) and stirred for 2.5 h. The reaction mixture was acidified with 1N HCl to pH 3 and concentrated in vacuo. The mixture was purified by chromatography on silica gel (CH3OH/HOAc/CH2Cl2 gradient 10/1/89 to 20/1/79) to give 124 mg (18%) of the title compound. MS calcd for C21H19N3O4 : 377, found 377.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe mixture was purified by chromatography on silica gel (CH3OH/HOAc/CH2Cl2 gradient 10/1/89 to 20/1/79)

출처 및 근거

ORD 기록
ord-a6f38ce5cd6f4a96aecc0ccb8e43b71b
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05314886

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