HCID 86622391, compound → HCID 68617178, compound

HRID 1158397Notes

Reaction equation

HRID 1158397 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=2)[CH:15]([CH3:17])[CH3:16])[C@H:10]([CH2:34][N:35]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=2)[CH:15]([CH3:16])[CH3:17])[C@H:10]([CH2:34][NH2:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86622391HCID 86622391, compound

Product 1

HCID 68617178HCID 68617178, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

According to the procedure described for Example 130/reaction step C, by hydrogenation of (3S,4R)-3-azidomethyl-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.95 g, 7.48 mmol), dissolved in absolute EtOH (100 mL), in the presence of Pd/C 10% (0.8 g; Engelhard 4505) at room temperature under atmospheric pressure to give, after filtration and drying in vacuo, the title compound as colorless oil. MS: 492.2 [M+H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.62 min.

Workup

  1. customto give
  2. filtrationafter filtration
  3. customdrying in vacuo
  4. customtR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min)
  5. custom4.62 min.

Sources & evidence

ORD record
ord-e871442e734b4d82a029cd124e46a7e5
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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