Water → (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide

HRID 454964노트

반응식

HRID 454964 반응식
[C:1]1([C@H:7]2[CH2:9][C@@H:8]2[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:23])[CH2:21][CH3:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>ClCCl.CN(C)C=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C@@H:20]([NH:23][C:10]([C@H:8]2[CH2:9][C@@H:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:12])[CH2:21][CH3:22])=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 7785172-Phenyl-1-cyclopropanecarboxylic acid, (1S-trans)-HCID 7127717(S)-1-(4-bromophenyl)propan-1-amine

생성물 1

HCID 67432459(1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide수율 92.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (1S,2S)-2-phenyl-cyclopropanecarboxylic acid (170 mg, 1.05 mmol) in dichloromethane (10 ml) was added oxallyl dichloride (145 mg, 1.2 mmol) followed by a few drops of N,N-dimethylformamide at RT. The reaction mixture was stirred at RT for 45 mins before it was concentrated down and dissolved in dichloromethane (1.5 ml). The solution was added slowly to a solution of (S)-1-(4-bromo-phenyl)-propylamine (250 mg, 1.0 mmol, HCl salt) and triethylamine (222 mg, 2.2 mmol) in dichloromethane (10 ml) at 0° C. The resulting reaction mixture was stirred at RT for 1.5 h. Water was added and the aqueous layer was extracted by dichloromethane. Organic layer was dried by magnesium sulfate and concentrated. The residue was purified via column chromatography on silica gel to afford (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide (330 mg, 92%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37 (d, J=8.6 Hz, 2H), 7.15-7.23 (m, 2H), 7.11 (d, J=7.3 Hz, 1H), 7.08 (d, J=8.3 Hz, 2H), 6.98 (d, J=7.3 Hz, 2H), 5.75 (d, J=7.6 Hz, 1H), 4.77 (q, J=7.5 Hz, 1H), 2.31-2.41 (m, 1H), 1.65-1.81 (m, 2H), 1.48-1.59 (m, 2H), 1.12-1.23 (m, 1H), 0.82 (t, J=7.4 Hz, 3H); LRMS (ESI) (M+1)=360.04. Molecular Formula=C19H20BrNO.

후처리

  1. concentrationwas concentrated down
  2. dissolutiondissolved in dichloromethane (1.5 ml)
  3. customThe resulting reaction mixture
  4. stirringwas stirred at RT for 1.5 h
  5. extractionthe aqueous layer was extracted by dichloromethane
  6. dry with materialOrganic layer was dried by magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography on silica gel

출처 및 근거

ORD 기록
ord-113f1d16fab24012a1c7329658d789c1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497271B2

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