methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate → methyl 2-((R)-((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamate

HRID 451906Notes

Reaction equation

HRID 451906 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:45])[NH:24][C@@H:25]([CH2:38][CH:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH2:26][N:27]([CH3:37])[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1>CO.[OH-].[OH-].[Pd+2]>[CH3:37][N:27]([CH2:26][C@@H:25]([NH:24][C:23]([N:19]1[CH2:20][CH2:21][CH2:22][C@@H:17]([C@H:8]([C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH2:18]1)=[O:45])[CH2:38][CH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29]

Participants

4

Reactant 1

HCID 68713077methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate

Product 1

HCID 68712425methyl 2-((R)-((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamateYield 21%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A 50 mL flask was charged with methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate (100 mg, 0.15 mmol) and Pd(OH)2 (20 mg) dissolved in MeOH (5 mL) under H2. After stirring for 0.5 hr, the mixture was filtered, evaporated to give crude methyl 2-((R)—((R)-1-((S)-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamate (20 mg, 21%), which was used without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-a12b4179123f4a50bb89f6504f25319b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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