HCID 86622394, compound → HCID 68618031, compound

HRID 1158405Notes

Reaction equation

HRID 1158405 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:30]([CH3:32])[CH3:31])[C:15](=[O:29])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:17]=2)[C@H:10]([CH2:33][N:34]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:30]([CH3:31])[CH3:32])[C:15](=[O:29])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:17]=2)[C@H:10]([CH2:33][NH2:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86622394HCID 86622394, compound

Product 1

HCID 68618031HCID 68618031, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

According to the procedure described for Example 130/reaction step C, by hydrogenation of (3S,4R)-3-azidomethyl-4-({isopropyl-[3-(3-methoxy-propoxy)-4-methyl-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.68 g, 7.31 mmol), dissolved in MeOH (80 mL), in the presence of Pd/C 10% (1.0 g; Engelhard 4505) at room temperature under atmospheric pressure to give, after filtration and drying in vacuo, the title compound as oil. MS: 478.2 [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): 4.28 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. custom4.28 min.

Sources & evidence

ORD record
ord-86302d61f58f4b8a9cf1b3b6ceddf442
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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