Triethylamine → HCID 22182443, compound

HRID 1796813Notes

Reaction equation

HRID 1796813 reaction equation
COC(=O)[CH2:4][N:5]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([O:38]CC2C=CC=CC=2)=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH:6]([C:20]12[O:27][CH2:26][C:23]([CH3:28])([CH2:24][O:25]1)[CH2:22][O:21]2)[CH:7]([NH:9][C:10]([O:12]CC1C=CC=CC=1)=O)[CH3:8].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[OH:38][C:35]1[CH:34]=[CH:33][C:32]([S:29]([N:5]2[CH:6]([C:20]34[O:27][CH2:26][C:23]([CH3:28])([CH2:22][O:21]3)[CH2:24][O:25]4)[CH:7]([CH3:8])[NH:9][C:10](=[O:12])[CH2:4]2)(=[O:31])=[O:30])=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69597607HCID 69597607, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22182443HCID 22182443, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of {(4-benzyloxy-benzenesulfonyl)-[2-benzyloxycarbonylamino-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-amino}-acetic acid methyl ester (compound of formula LIII, 1.3 g, 2.0 mmol) in 75 ml of ethanol was treated with triethylamine (0.28 ml, 0.20 g, 2.0 mmol) and 0.2 g of 10% palladium on carbon. After stirring for about 2 hours under 1 atmosphere of hydrogen, the mixture was filtered through a pad of Celite® and concentrated in vacuo. The residue was dissolved in 10 ml of toluene, diluted with 3 ml of methanol and was refluxed for about 1.5 hours. Concentration of the mixture in vacuo afforded 0.6 g of 4-(4-hydroxy-benzenesulfonyl)-6-methyl-5-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-piperazin-2-one (compound of formula LIV). A compound of the formula LI can be converted to a compound of the formula LIII by the method of Step 42 that, in turn, can be converted to a compound of Formula I according to the procedure of Step 43.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 10 ml of toluene
  4. additiondiluted with 3 ml of methanol
  5. temperaturewas refluxed for about 1.5 hours

Sources & evidence

ORD record
ord-7f9a697cca194418b4850a2b05fba815
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

Loading…