HCID 68542589, compound → HCID 68542695, compound

HRID 1432079Notes

Reaction equation

HRID 1432079 reaction equation
[Cl:1][CH2:2][CH:3]([CH:5]1[NH:20][C:19](=[O:21])[C@H:18]([CH3:22])[N:17]([CH3:23])[C:16](=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8][C@@H:7]([CH3:25])[CH2:6]1)[OH:4]>CCO.[Pd]>[Cl:1][CH2:2][CH:3]([CH:5]1[NH:20][C:19](=[O:21])[C@H:18]([CH3:22])[N:17]([CH3:23])[C:16](=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]([CH3:25])[CH2:6]1)[OH:4]

Participants

4

Reactant 1

HCID 68542589HCID 68542589, compound

Product 1

HCID 68542695HCID 68542695, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.24 g (3.32 mmol) of (E)-(3S,14R)-16-(2-chloro-1-hydroxy-ethyl)-3,4,14-trimethyl-1,4diaza-cyclohexadec-10-ene-2,5-dione in 33 ml EtOH is stirred at rt in the presence of 332 mg 10% Pd/C under a hydrogen atmosphere for 1 h. More catalyst is added (332 mg) and the hydrogenation is continued for 4 h. The catalyst is filtered off and the filtrate evaporated. The residue is purified by chromatography on silica gel (DCM/methanol 95/5) and gives the title compound as a brownish foam (mixture of diastereomers).

Workup

  1. additionMore catalyst is added (332 mg)
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate evaporated
  4. customThe residue is purified by chromatography on silica gel (DCM/methanol 95/5)

Sources & evidence

ORD record
ord-6a43656f5a7d4b1989d30e1832d9821c
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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