Ethanol → HCID 178478661, compound

HRID 849154Notes

Reaction equation

HRID 849154 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]1[NH:16][C:15](=[NH:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)C.[H][H]>Cl.[Pt]=O>[ClH:1].[ClH:1].[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH:10]1[NH:16][C:15](=[NH:17])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 702EthanolHCID 178418361HCID 178418361, compoundHCID 178479063HCID 178479063, compound

Product 1

HCID 178478661HCID 178478661, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolvent2×

Procedure

The product of Example 290 (138 mg, 0.5 mmol), platinum oxide (100 mg), conc HCl (0.5 mL) and ethanol (30 mL) were shaken on a Parr hydrogenator at 55 psi of hydrogen overnight. Filtration and concentration in vacuo gave a colorless oil. The oil was purified by C-18 reverse phase chromatography eluting with a CH3CN/H2O (0.05% TFA) gradient to give a white solid. The solid was dissolved in 1N HCl and lyophilized to afford the title product as a colorless foam (81 mg, 55% yield).

Workup

  1. filtrationFiltration and concentration in vacuo
  2. customgave a colorless oil
  3. customThe oil was purified by C-18 reverse phase chromatography
  4. washeluting with a CH3CN/H2O (0.05% TFA) gradient
  5. customto give a white solid

Sources & evidence

ORD record
ord-f0f353cbeef44c0a90bfdf1b6de1cc71
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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