HCID 68712444, compound → HCID 46224954, compound

HRID 451898Notes

Reaction equation

HRID 451898 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([C@H:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[O:32][CH2:33][CH2:34][NH:35][C:36](=[O:39])[O:37][CH3:38])[CH2:26]2)=[O:24])[CH2:9][N:10](C)[C:11](OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:7][C@H:8]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([C@H:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[O:32][CH2:33][CH2:34][NH:35][C:36](=[O:39])[O:37][CH3:38])[CH2:26]2)=[O:24])[CH2:9][NH:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68712444HCID 68712444, compound

Product 1

HCID 46224954HCID 46224954, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A 100 mL flask was charged with methyl 2-((R)—((R)-1-((S)-1-cyclohexyl-3-(N-methyl-N-(benzyloxycarbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamate (230 mg, 0.35 mmol) and Pd(OH)2 (45 mg) dissolved in MeOH (35 mL) under H2 and stirred for 1 hr. After completion of the reaction, the mixture was filtered. The solution was evaporated to give the crude product (120 mg), which was purified by preparative HPLC to obtain the target molecule (50.2 mg, 29%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered
  3. customThe solution was evaporated

Sources & evidence

ORD record
ord-9b3f784aedfd45acb4f837b92bff3bf1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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