HCID 57835491, compound → HCID 57835513, compound

HRID 731165Notes

Reaction equation

HRID 731165 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:42])[C@H:11]([CH:39]([CH3:41])[CH3:40])[CH2:12][C@H:13]([OH:38])[C@@H:14]([N:35]=[N+]=[N-])[CH2:15][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[CH:17]([CH3:19])[CH3:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[N:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:42])[C@H:11]([CH:39]([CH3:41])[CH3:40])[CH2:12][C@H:13]([OH:38])[C@@H:14]([NH2:35])[CH2:15][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[CH:17]([CH3:19])[CH3:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57835491HCID 57835491, compound

Product 1

HCID 57835513HCID 57835513, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (Pd/C) 10% (200 mg) is added to a solution of (2S,4S,5S,7S)-5-azido4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-piperidin-1-yl-ethyl)-amide (780 mg, 1.32 mmol) in MeOH (40 mL) under Ar. Then the reaction suspension is stirred under a atmosphere of hydrogen (H2) for 8 hours. The catalyst is filtered-off over Celite and washed with MeOH. Evaporation of the solvent gives the crude product which is pure according to anaylsis and used without further purification. MS (LC-MS): 564.1 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 minutes, 100% CH3CN/3 minutes, 100-10% CH3CN/H2O/3 minutes, flow: 1.5 mL/min.): 4.31 minutes.

Workup

  1. washwashed with MeOH
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fa37bcc8e2d246f4bb2ab7c5f9f579f9
Source dataset
uspto-grants-2009_09
Patent number
US07582782B2

Reaction notes

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