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

HRID 2173357Notes

Reaction equation

HRID 2173357 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[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;

Workup

  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

Sources & evidence

ORD record
ord-7e7cc37e434f4c9ea04bcec500c5b959
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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