Dimethyl Sulfoxide → 2-[2-(4-Fluorophenyl)-2-oxoethyl]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

HRID 18795ノート

反応式

HRID 18795 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:44])[CH2:19][C:20]2[N:21]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:44])[CH2:19][C:20]2[N:21]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[C@H:22]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86596336HCID 86596336、化合物

生成物 1

HCID 865963372-[2-(4-Fluorophenyl)-2-oxoethyl]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester収率 89.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cold (−70° C.) solution of oxalyl chloride (0.27 mL, 3.06 mmol) in dichloromethane (15 mL) is added DMSO (0.32 mL, 6.11 mmol) followed by the alcohol 256 (1.28 g, 2.48 mmol) in dichloromethane (5 mL). The mixture is stirred for at −70° C. solution 15 min., and triethylamine (1.03 mL, 13.9 mmol) is added and the mixture is allowed to come to RT and is stirred for 4 h. The reaction mixture is washed with water, brine, then dried (MgSO4), and filtered. The filtrate is rotary evaporated, and the residue is recrystallized from Et2O to give 1.02 g of the product 257. 1H NMR (CDCl3) δ 10.60 (s, 1 H), 8.10-7.95 (m, 2 H), 7.10-6.90 (m, 12 H), 6.90-6.70 (m, 2 H), 5.40 (s, 2 H), 1.25 (s, 9 H); MS: m/z 459 (M++1).

後処理

  1. additionis added
  2. customto come to RT
  3. washThe reaction mixture is washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe residue is recrystallized from Et2O

出典と根拠

ORDレコード
ord-0ef742bc98a94273aeeb71707fcbd7c5
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

反応ノート

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