HCID 90937696, compound → HCID 21094555, compound

HRID 1350918Notes

Reaction equation

HRID 1350918 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:34])[CH2:16][NH:17][C:18]([CH3:33])([CH3:32])[CH2:19][CH2:20][N:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:23]=[CH:22]2)=[CH:11][C:10]=1[NH:35][S:36]([C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:48]=1[NH:47][CH2:46][CH2:45][CH2:44]2)(=[O:38])=[O:37])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:33][C:18]([NH:17][CH2:16][C@@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:35][S:36]([C:39]2[CH:40]=[CH:41][CH:42]=[C:43]3[C:48]=2[NH:47][CH2:46][CH2:45][CH2:44]3)(=[O:37])=[O:38])[CH:11]=1)[OH:34])([CH3:32])[CH2:19][CH2:20][N:21]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]=[CH:22]1

Participants

5

Reactant 2

HCID 90937696HCID 90937696, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21094555HCID 21094555, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.10 g palladium (5% on activated charcoal) were added to a solution of 0.20 g (0.41 mmol) (R)-1,2,3,4-tetrahydro-quinoline-8-sulphonic acid (2-benzyloxy-5-{2-[1,1-dimethyl-3-(4-phenyl-imidazol-1-yl)-propylamino]-1-hydroxy-ethyl}-phenyl)-amide in 20 mL ethanol. The reaction mixture was shaken in an autoclave under a hydrogen pressure of 20 psi at ambient temperature for 6 h. The hydrogen pressure was released, the palladium filtered off and the filtrate was freed from solvent using the rotary evaporator. The residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]. 0.20 g (0.31 mmol, 75%) (R)-1,2,3,4-tetrahydro-quinoline-8-sulphonic acid(5-{2-[1,1-dimethyl-3-(4-phenyl-imidazol-1-yl)-propylamino]-1-hydroxy-ethyl}-2-hydroxy-phenyl)-amide were obtained as a colourless solid.

Workup

  1. filtrationthe palladium filtered off
  2. customthe rotary evaporator
  3. customThe residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]

Sources & evidence

ORD record
ord-457758f1245d4667bceec5c4c54f1e53
Source dataset
uspto-grants-2007_05
Patent number
US07214698B2

Reaction notes

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