Hydrochloric Acid → 4-Oxo-4-{4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yl}-butyric acid

HRID 746790

反応式

HRID 746790 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)O1.Br[C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].O.[OH-].[Na+].Cl>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:41]=[C:35]([C:32]1[CH:33]=[CH:34][C:29]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:23])=[CH:13][CH:14]=2)=[CH:30][CH:31]=1)[CH2:36][CH2:37][C:38]([OH:40])=[O:39]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 806463-(4-Bromobenzoyl)propionic acidHCID 2735133Sodium Carbonate MonohydrateHCID 59747992Propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide

生成物 1

HCID 692513514-Oxo-4-{4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yl}-butyric acid

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Heat in a sealed tube with stirring propane-2-sulfonic acid{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (0.5 mmol), 4-(4-Bromo-phenyl)-4-oxo-butyric acid (0.75 mmol), 2M Na2CO3 water solution (0.2 mL) and Pd(PPh3)4 (0.05 mmol) in 4.0 ml of an anhydrous DME to 100° C. for 24 h. Evaporate and purify the filtrate by flash chromotography (Silica gel-hexane/EtOAc). Add NaOH 2M (1 ml) to a suspension of the resultant ester (0.128 mmol) in ethanol (1 ml) and stir 24 h. Add 6N HCl until pH is approximately 1 and a white solid precipitates. Filter the solid to provide the title compound. MS (ES−): 456 (M−1).

後処理

  1. customEvaporate
  2. custompurify the filtrate by flash chromotography (Silica gel-hexane/EtOAc)
  3. customa white solid precipitates
  4. filtrationFilter the solid

出典と根拠

ORDレコード
ord-225767fe43c844488612b31349ac800e
出典データセット
uspto-grants-2008_07
特許番号
US07393868B2

関連ノート

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