Dicyclohexylcarbodiimide → (E)-S-4-fluorophenyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

HRID 2368878ノート

反応式

HRID 2368878 の反応式
[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:16]([CH3:25])[CH:15]=2)[CH:11]=1)[C:6]([OH:8])=O.C1CCC(N=C=NC2CCCCC2)CC1.[F:42][C:43]1[CH:48]=[CH:47][C:46]([SH:49])=[CH:45][CH:44]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10](/[CH:12]=[CH:13]/[C:14]2[CH:15]=[C:16]([CH3:25])[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:18]([CH3:20])[CH:19]=2)[CH:11]=1)[C:6](=[O:8])[S:49][C:46]1[CH:47]=[CH:48][C:43]([F:42])=[CH:44][CH:45]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 677894-FluorothiophenolHCID 67262210(E)-3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

生成物 1

HCID 86672879(E)-S-4-fluorophenyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of Compound 5 (80 mg, 0.225 mmol) in DCM (3 mL) were added DCC (70 mg, 0.338 mmol), DMAP (5.5 mg, 0.045 mmol), and 4-fluorobenzenethiol (37 μL, 0.338 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) and filtered through Celite. The filtrate was washed with brine, and dried with Na2SO4. The solution was filtered and concentrated. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=8/1) to give (E)-S-4-fluorophenyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate.

後処理

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-cdee8970961645e7b1d5ac5e5a26ec0e
出典データセット
uspto-grants-2014_04
特許番号
US08703815B2

反応ノート

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