HCID 72465841, compound → HCID 69367981, compound

HRID 851956Notes

Reaction equation

HRID 851956 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([N:20]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[C:11]=1[CH3:19])=O)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C@H:5]1[CH2:6][CH2:7][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[C:11]=2[CH3:19])[NH:20]1)=[O:34])[CH3:2]

Participants

4

Reactant 1

HCID 72465841HCID 72465841, compound

Product 1

HCID 69367981HCID 69367981, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(benzhydrylideneamino)-5-(4-methoxy-2,3-dimethylphenyl)-5-oxopentanoic acid ethyl ester (16.56 mmol) in EtOH (80 mL) containing 10% Pd/C (760 mg) is stirred under an atmosphere of H2 (double-stuffed balloon) for 18 h. The reaction mixture is then filtered through of pad of Celite using MeOH for the rinse. The filtrated is concentrated in vacuo to a nearly colorless syrup, which is used in the next reaction without further purification. 1H NMR (CDCl3, 400 MHz): 7.46 (d, J=8.6 Hz, 1H), 6.75 (d, J=8.6 Hz, 1H), 4.40 (dd, J=8.8, 6.6 Hz, 1H), 4.23 (q, J=8.8 Hz, 2H), 3.90 (dd, J=8.6, 5.4 Hz, 1H), 3.82 (s, 3H), 2.29 (s, 3H), 2.19 (s, 3H), 2.25-2.05 (m, 4H), 1.72-1.65 (m, 1H), 1.31 (t, J=8.8 Hz, 3H). Electrospray MS: m/z 278 [M+1].

Workup

  1. filtrationThe reaction mixture is then filtered through of pad of Celite
  2. concentrationThe filtrated is concentrated in vacuo to a nearly colorless syrup, which
  3. customis used in the next reaction without further purification

Sources & evidence

ORD record
ord-b8efd55456444ec7b775b93dadec994b
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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