1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9948631, compound

HRID 434065Notes

Reaction equation

HRID 434065 reaction equation
CO[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([N+:23]([O-:25])=[O:24])=[CH:15][CH:14]=1)=[O:11])=[O:4].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N+:23]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([N:12]2[C:3](=[O:4])[CH:5]3[CH2:9][CH2:8][CH2:7][N:6]3[C:10]2=[O:11])=[CH:14][CH:15]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 16098447HCID 16098447, compound

Product 1

HCID 9948631HCID 9948631, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of compound 2A (410 mg, 1.29 mmol) and DBU (0.2 mL, 1.33 mmol) in toluene (10 mL) was heated at 80° C. for 2 hours. HPLC check of the reaction showed little product formed. Additional DBU (0.1 mL) was added and the reaction heated at 90° C. overnight. After cooling to RT, the reaction mixture was filtered. The filtrate was diluted with EtOAc, washed with 1 N aqueous HCl, water, brine, dried over MgSO4 and concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with CH2Cl2, 0.2% to 0.4% MeOH in CH2Cl2 to give the title compound (racemate) (80 mg) as a brown solid. mp. 215-217° C. HPLC: 97.5% at 2.51 min (retention time) (YMC S5 ODS column 4.6×50 mm; 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nM), MS (ES): m/z 312 [M+1]+.

Workup

  1. customformed
  2. temperaturethe reaction heated at 90° C. overnight
  3. temperatureAfter cooling to RT
  4. filtrationthe reaction mixture was filtered
  5. additionThe filtrate was diluted with EtOAc
  6. washwashed with 1 N aqueous HCl, water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customto give a crude product, which
  10. customwas chromatographed (silica gel)
  11. washeluting with CH2Cl2, 0.2% to 0.4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-93c1603f5aa64579a02c0f28c696aa26
Source dataset
uspto-grants-2003_12
Patent number
US06670386B2

Reaction notes

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