Hydrochloric Acid → HCID 42623936, compound

HRID 1925510Notes

Reaction equation

HRID 1925510 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[CH:14]=[C:15]([CH2:19][CH2:20][NH:21][CH2:22][C@@H:23]([C:25]4[CH:34]=[CH:33][C:32]([O:35]CC5C=CC=CC=5)=[C:31]5[C:26]=4[CH:27]=[CH:28][C:29](=[O:43])[NH:30]5)[OH:24])[CH:16]=[CH:17][CH:18]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl>CO.O1CCCC1.[Pd]>[C:1]12([CH2:11][O:12][C:13]3[CH:14]=[C:15]([CH2:19][CH2:20][NH:21][CH2:22][C@@H:23]([C:25]4[CH:34]=[CH:33][C:32]([OH:35])=[C:31]5[C:26]=4[CH:27]=[CH:28][C:29](=[O:43])[NH:30]5)[OH:24])[CH:16]=[CH:17][CH:18]=3)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67520511HCID 67520511, compound

Product 1

HCID 42623936HCID 42623936, compoundYield 86.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 43 (0.075 g, 0.13 mmol) in a mixture of methanol (3 mL) and tetrahydrofuran (1 mL) was added some drops of hydrogen chloride 1.25M in methanol and palladium on charcoal (10%, 0.015 g). The reaction mixture was hydrogenated under a balloon pressure overnight. The catalyst was filtered through Celite® and the solvent removed under reduced pressure. The crude was treated with ether and collected by filtration to obtain the title compound as a yellow solid (0.055 g, 82%).

Workup

  1. customwas hydrogenated under a balloon pressure overnight
  2. filtrationThe catalyst was filtered through Celite®
  3. customthe solvent removed under reduced pressure
  4. additionThe crude was treated with ether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ff945684fa924b95a833b5084baf8220
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

Loading…