Triethylamine → HCID 67086573, 화합물

HRID 2174971노트

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HRID 2174971 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([C:22](Cl)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C:22]([C:17]3[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:23])[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate2회

생성물 1

HCID 67086573HCID 67086573, 화합물수율 68.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3,8-Diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (Intermediate 1, 300 mg, 1.42 mmol), biphenyl-2-carbonyl chloride (429 mg, 1.98 mmol) and tri-ethyl amine (0.6 mL, 3.95 mmol) were dissolved into DCM (5 mL) and stirred at room temperature for 18 h. The reaction mixture was diluted with DCM (25 mL) and washed with 1N NaOH (10 mL) and water (2×20 mL). The organic layers were combined, dried, filtered and concentrated under reduced pressure to yield 8-(Biphenyl-2-carbonyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (380 mg, 68.6%). MS (ESI) mass calcd. for C24H28N2O3, 392.49; m/z found, 293.2 [M+H]+ (mass without Boc group). 1H NMR (CDCl3): 7.57-7.30 (m, 9H), 4.60-4.35 (m, 0.5H), 4.17-3.98 (m, 0.5H), 3.90-3.71 (m, 1H), 3.60-3.25 (m, 3H), 3.22-2.66 (m, 2H), 2.54-2.38 (m, 0.5H), 2.37-2.22 (m, 0.5H), 2.10-1.92 (m, 0.5H), 1.85-1.56 (m, 1.5H), 1.55-1.27 (m, 9H).

후처리

  1. washwashed with 1N NaOH (10 mL) and water (2×20 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b145679275254e0086af1516581d6e9b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062044B2

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