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

HRID 2053588노트

반응식

HRID 2053588 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, 1H), 8.10-7.95 (m, 2H), 7.10-6.90 (m, 12H), 6.90-6.70 (m, 2H), 5.40 (s, 2H), 1.25 (s, 9H); 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-56b4af73d0414ff9ac7615c7c88199b9
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326792B2

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