1,2-Dichloroethane → Benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 2173357노트

반응식

HRID 2173357 반응식
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[CH:16]12[CH2:22][CH:19]([NH:20][CH2:21]1)[CH2:18][N:17]2[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][C:13]([N:20]3[CH2:21][CH:16]4[CH2:22][CH:19]3[CH2:18][N:17]4[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[O:15])=[CH:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 841658(4-Tetrazol-1-yl-phenyl)-acetic acidHCID 2760899Benzyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

생성물 1

HCID 67518237Benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[4-(1H-Tetrazol-1-yl)phenyl]acetic acid (303 mg, 1.48 mmol) was combined with benzyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (399 mg, 1.48 mmol), EDC (341 mg, 1.78 mmol), and triethylamine (0.248 mL, 1.78 mmol) in DCM (30 mL) and stirred overnight at room temperature. The mixture was washed with 1 M HCl solution, saturated sodium bicarbonate solution, and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by MPLC eluting with a 0-5% gradient of methanol in ethyl acetate to afford benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate. LC/MS: [(M+1)]+=419;

후처리

  1. washThe mixture was washed with 1 M HCl solution, saturated sodium bicarbonate solution, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by MPLC
  6. washeluting with a 0-5% gradient of methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-7e7cc37e434f4c9ea04bcec500c5b959
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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