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Hydrochloric Acid → 4-chloro-N-[4-(5-hydroxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 852000
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HRID 852000 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([CH2:32][O:33]C(=O)C)[O:29][N:28]=3)=[CH:23][CH:22]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([CH2:32][OH:33])[O:29][N:28]=3)=[CH:23][CH:22]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:9])=[O:10])=[CH:6][CH:7]=1
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반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69489530Acetic acid 3-(4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-[1,2,4]oxadiazol-5-ylmethyl ester

생성물 1

HCID 694924154-chloro-N-[4-(5-hydroxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 0.03 g (0.05 mmol) acetic acid 3-(4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-[1,2,4]oxadiazol-5-ylmethyl ester in 1 ml tetrahydrofuran was stirred with 0.2 ml (0.2 mmol) 1 molar aqueous sodium hydroxide for 3 hours at room temperature. Water and aqueous hydrochloric acid was added to reach pH 1. Extraction with ethylacetate, drying with sodium sulfate, filtration and removal of the solvent by distillation yielded 0.02 g (98%) 4-chloro-N-[4-(5-hydroxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=491.0 (MH+, 100).

후처리

  1. extractionExtraction with ethylacetate
  2. dry with materialdrying with sodium sulfate, filtration and removal of the solvent by distillation

출처 및 근거

ORD 기록
ord-afd867d41a064c4fa4fa85dd1bab2061
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253158B2

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