1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86681594, compound

HRID 1912365Notes

Reaction equation

HRID 1912365 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:23]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1>C1COCC1>[NH2:23][C@H:16]([C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131731086HCID 131731086, compound

Product 1

HCID 86681594HCID 86681594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 61 (1.50 g, 2.75 mmol) in THF (20 mL) was added DBU (1.5 mmol, 229 μL). After 10 minutes, TLC analysis indicated complete consumption of starting material. 1 M aq. HCl (30 mL) and EtOAc (25 mL) were added and the layers were separated. The organic layer was extracted with 1 M aq. HCl and the combined aqueous layers were basified with Na2CO3 until pH 10. This layer was extracted with EtOAc (3×) and the latter combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained as a colorless oil (yield: 0.75 g, 2.34 mmol, 85%). 1H NMR (400 MHz, CDCl3) δ=7.62 (s, 1H), 7.33 (d, J=8.14 Hz, 2H), 7.09 (d, J=8.43 Hz, 2H), 4.02-3.95 (m, 1H). 3.57 (s, 3H), 3.16 (s, 3H), 2.98 (dd, J=13.30, 5.56 Hz, 1H), 2.65 (dd, J=13.25, 7.71 Hz, 1H), 1.93 (s, 2H), 1.49 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3) δ=175.13, 152.66, 137.04, 131.64, 129.29, 118.28, 79.54, 60.96, 52.38, 40.41, 31.82, 27.94 ppm. [α]D23=+19.6 (c=1, CHCl3). HRMS: calcd. for C16H25N3O4 324.19178 [M+H]+. found 324.19193.

Workup

  1. customconsumption of starting material
  2. addition1 M aq. HCl (30 mL) and EtOAc (25 mL) were added
  3. customthe layers were separated
  4. extractionThe organic layer was extracted with 1 M aq. HCl
  5. extractionThis layer was extracted with EtOAc (3×)
  6. dry with materialwere dried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81fe4d9890334ead93871b190a0c0746
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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