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

HRID 2173357ノート

反応式

HRID 2173357 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

[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;

後処理

  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

出典と根拠

ORDレコード
ord-7e7cc37e434f4c9ea04bcec500c5b959
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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