HCID 91428272, compound → HCID 86588608, compound

HRID 2416737Notes

Reaction equation

HRID 2416737 reaction equation
[N+](C1C=CC(COC([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:44]=[CH:43][C:20]3[CH2:21][C@@H:22]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:23](=[O:37])[N:24]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH2:25][C:19]=3[CH:18]=2)=O)=CC=1)([O-])=O>CO.[Pd]>[NH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:44]=[CH:43][C:20]2[CH2:21][C@@H:22]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:23](=[O:37])[N:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[CH2:25][C:19]=2[CH:18]=1

Participants

4

Reactant 1

HCID 91428272HCID 91428272, compound

Product 1

HCID 86588608HCID 86588608, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To methyl (S)-8-[3-(4-nitrobenzyloxycarbonylamino)-1-propyloxy]-3-oxo-2-[4-(trifluoromethyl)benzyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.12 g, 0.19 mmol) in MeOH (2 mL) was added 10% Pd/C (20 mg). The reaction vessel was flushed with hydrogen and then fitted with a hydrogen-filled balloon. After 4.5 h, the hydrogen was vented and the catalyst was removed by filtration through celite®. Removal of solvent gave the title compound (0.09 g) as a pale yellow residue. This material was used without further purification. MS (ES) m/e 465.3 (M+H)+.

Workup

  1. customThe reaction vessel was flushed with hydrogen
  2. customfitted with a hydrogen-
  3. additionfilled balloon
  4. customthe catalyst was removed by filtration through celite®
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-60e43d72db4f47aebf394921747142b3
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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