Triethylamine → HCID 178424338, compound

HRID 967798Notes

Reaction equation

HRID 967798 reaction equation
C([O:8][C:9](=O)[CH2:10][C:11](=O)[CH2:12][O:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)C1C=CC=CC=1.Cl.[C:27]1([CH3:35])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][NH2:34].CCN(CC)CC.N12CCCN=C1CCCCC2>CCO.CN(C=O)C>[C:14]12([O:13][CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[N:33]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[CH3:35])[N:34]=3)[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 697440854-(Adamantan-1-yloxy)-3-oxo-butyric acid benzyl ester

Product 1

HCID 178424338HCID 178424338, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(adamantan-1-yloxy)-3-oxo-butyric acid benzyl ester (334 mg, 0.98 mmol), o-tolyl hydrazine hydrochloride (163 mg, 1.0 mmol), and NEt3 (140 μL, 1.0 mmol) in EtOH (6 mL) was stirred at room temperature for 1 hr. The mixture was evaporated and the residue partitioned between EtOAc (40 mL) and H2O (40 mL). The organic phase was separated, washed with brine (20 mL), and dried (MgSO4). Filtration and evaporation of the solvent gave the crude hydrazone. 1,8-Diazabicyclo[5.4.0]undec-7-ene (150 μl, 1.0 mmol) was added to a solution of the hydrazone in DMF (4 mL), and the solution stirred at room temperature for 17 h. The mixture was partitioned between 5% KHSO4 (60 mL) and EtOAc (60 mL). The organic layer was washed with brine (2×30 mL), and dried (MgSO4). Filtration and evaporation of the solvent gave the product as a solid which was triturated with ether, isolated by filtration and dried (170 mg, 51%).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between EtOAc (40 mL) and H2O (40 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation of the solvent
  7. customgave the crude hydrazone
  8. stirringthe solution stirred at room temperature for 17 h
  9. customThe mixture was partitioned between 5% KHSO4 (60 mL) and EtOAc (60 mL)
  10. washThe organic layer was washed with brine (2×30 mL)
  11. dry with materialdried (MgSO4)
  12. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-1965f94bfde54538a738a45a6e7d25e9
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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