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1,1'-Carbonyldiimidazole → 3,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-(phenylmethyl)benzenepropanamide

HRID 2256315
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HRID 2256315 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:18])=[O:16])[CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:14][C:15]([N:17]([CH3:18])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 190293143,4-Dichloro-beta-[2-[(phenylmethyl)methylamino]-2-oxoethyl]benzenepropanoic acid

생성물 1

HCID 190293813,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-(phenylmethyl)benzenepropanamide수율 94.6%

시약·촉매·용매 2

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매
2회

실험 절차

3,4-Dichloro-beta-[2-[(phenylmethyl)methylamino]-2-oxoethyl]benzenepropanoic acid (6.9 g) in EtOAc (150 mL) was treated with carbonyldiimidazole (4.4 g) and N,N-dimethylaminopyridine (0.22 g). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for 1 hour. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (4.46 g) in H2O (75 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with EtOAc (250 mL) and washed with 1N HCl (250 mL), H2O (250 mL) and dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound (6.29 g).

후처리

  1. temperatureheated at 50° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with 1N HCl (250 mL), H2O (250 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-134fadaa76494e69ad4d76e6b7e8b8d7
출처 데이터셋
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05654316

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