1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

HRID 227345Notes

Reaction equation

HRID 227345 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]([O:20][CH:21]([O:28][C:29]([NH:31][CH2:32][C:33]1([CH2:39][C:40]([O:42]CCC#N)=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:12]([O:20][CH:21]([O:28][C:29]([NH:31][CH2:32][C:33]1([CH2:39][C:40]([OH:42])=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 66810793HCID 66810793, compound

Product 1

HCID 116115921-[{(alpha-Benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic AcidYield 4.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

DBU (79.2 mg, 78 μL, 0.520 mmol) was added to a solution of 2-cyanoethyl 1-{[(α-benzoyloxybenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetate (11) (166 mg, 0.347 mmol) in 10 mL of CH2Cl2 at −10° C. The reaction mixture was stirred at 0° C. for 1 hour, then allowed to warm to room temperature, stirred for two hours and cooled to 0° C. Another 78 μL of DBU was added, the reaction mixture was stirred for 3 hours at 0° C. and then allowed to warm to room temperature. The reaction mixture was diluted with CH2Cl2, washed with citric acid and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by reversed phase HPLC to afford 7 mg (4.7%) of the title compound. M.p. 75.5-76.0° C. 1H NMR (CDCl3): δ 8.08 (2H, dd, J=8.8, 1.2 Hz); 7.89 (1H, s); 7.63-7.55 (3H, m); 7.46-7.26 (5H, m); 5.38 (1H, t, J=6.8 Hz); 3.26 (2H, dd, J=6.8, 0.8 Hz); 2.34 (2H, s); 1.58-1.35 (10 H, m). MS (ESI) m/z 424 (M−H31 ).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for two hours
  3. temperaturecooled to 0° C
  4. stirringthe reaction mixture was stirred for 3 hours at 0° C.
  5. temperatureto warm to room temperature
  6. washwashed with citric acid and brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-0d812e0c7087424aa621bb3b9a5d54c0
Source dataset
uspto-grants-2009_07
Patent number
US07560483B2

Reaction notes

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