Hydrochloric Acid → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamate

HRID 856188노트

반응식

HRID 856188 반응식
N1C=CC=CC=1.ClC(Cl)(O[C:11](=[O:17])[O:12][C:13](Cl)(Cl)Cl)Cl.OC[C@:21]1([CH3:32])[O:25][C:24]2=[N:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][N:23]2[CH2:22]1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)=[CH:36][CH:35]=1.Cl>C(Cl)Cl>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[C:11](=[O:17])[O:12][CH2:13][C@:21]2([CH3:32])[O:25][C:24]3=[N:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][N:23]3[CH2:22]2)=[CH:36][CH:35]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 94429TriphosgeneHCID 234111Bis(p-chlorophenyl)amineHCID 26596862(r)-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanol

생성물 1

HCID 69481080(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamate수율 35.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Pyridine (0.37 ml, 4.5 mmol) and triphosgene (0.16 g, 0.5 mmol) were added to a suspension of (R)-2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 37 (0.30 g, 1.5 mmol) in methylene chloride (15 ml) with cooling on ice-bath followed by stirring at room temperature for 2.5 hours. To the reaction mixture, bis(4-chlorophenyl)amine (0.39 g, 1.6 mmol) was added, and the resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was cooled on ice-bath and added 10% hydrochloric acid. The resulting mixture was extracted with methylene chloride, and the extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silicagel column chromatography (methylene chloride/ethyl acetate=19/1) and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl bis(4-chlorophenyl)carbamate (82 mg, yield 12%) as a white solid.

후처리

  1. temperaturewith cooling on ice-bath
  2. stirringthe resulting mixture was stirred at room temperature for 20 hours
  3. temperatureThe reaction mixture was cooled on ice-bath
  4. extractionThe resulting mixture was extracted with methylene chloride
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silicagel column chromatography (methylene chloride/ethyl acetate=19/1)
  8. customrecrystallized from isopropanol

출처 및 근거

ORD 기록
ord-83cb12cfe28846a3b2a4a03eca321d87
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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