Triethylamine → HCID 68429408, compound

HRID 1931292Notes

Reaction equation

HRID 1931292 reaction equation
C(N(CC)CC)C.Cl[C:9]1[S:10][C:11](Cl)=[CH:12][C:13]=1[S:14]([N:17]1[CH2:22][C@H:21]2[CH2:23][CH2:24][C@@H:18]1[C@H:19]([C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=1)=[O:26])[CH2:20]2)(=[O:16])=[O:15].[H][H]>[OH-].[Pd+2].[OH-].[C].CO>[CH:35]([O:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:25]([C@H:19]2[C@H:18]3[CH2:24][CH2:23][C@H:21]([CH2:22][N:17]3[S:14]([C:13]3[CH:12]=[CH:11][S:10][CH:9]=3)(=[O:15])=[O:16])[CH2:20]2)=[O:26])=[CH:29][CH:30]=1)([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68430505HCID 68430505, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68429408HCID 68429408, compound

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

Triethylamine (0.065 mL, 0.42 mmol) and 20% palladium hydroxide-carbon catalyst (8 mg) were added to a methanol (2 mL) solution of the compound (35 mg, 0.0695 mmol) synthesized in Example 25, and the mixture was stirred for 5 hours in a hydrogen (4 atm) atmosphere. The reaction mixture was then celite filtered, and the filtrate was concentrated. The resulting residue was then purified using silica gel column chromatography to obtain the target (9.9 mg, 33%).

Workup

  1. concentrationcelite filtered, and the filtrate was concentrated
  2. customThe resulting residue was then purified
  3. customto obtain the target (9.9 mg, 33%)

Sources & evidence

ORD record
ord-808ad08c9f2e4bed94be664cd490833f
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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