HCID 60206120, compound → HCID 22176233, compound

HRID 1797739Notes

Reaction equation

HRID 1797739 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:12](=[O:33])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:34][CH:35]([CH3:36])[CH3:37])[C:12](=[O:33])[C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][C:16]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:15][CH:14]=2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 1

HCID 60206120HCID 60206120, compound

Product 1

HCID 22176233HCID 22176233, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl (E)-3-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)-2-propenoate (0.90 g, 1.8 mmol) and 5% palladium carbon (0.5 g) in ethanol (10 ml) and tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere at room temperature for 2 h. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ethyl 3-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)propanoate (0.82 g, 90.1%) as an amorphous solid. 1H-NMR(CDCl3) δ: 0.99 (6H, d, J=6.6 Hz), 1.19 (3H, t, J=7.1 Hz), 1.42 (9H, s), 2.18–2.29 (1H, m), 2.51 (2H, t, J=7.8 Hz), 2.90 (2H, t, J=7.8 Hz), 4.01–4.12 (4H, m), 4.19 (2H, d, J=5.6 Hz), 4.40 (1H, bs), 6.74 (1H, d, J=1.6 Hz), 7.21–7.26 (2H, m), 7.31 (1H, dd, J=1.6, 8.4 Hz), 7.46–7.53 (3H, m), 8.39 (1H, d, J=8.4 Hz).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bab76f183024fc8bbabf962e9997858
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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