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

HRID 18795노트

반응식

HRID 18795 반응식
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

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86596336HCID 86596336, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ef742bc98a94273aeeb71707fcbd7c5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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