(S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamate → methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate

HRID 451894Notes

Reaction equation

HRID 451894 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][C@H:5]([NH:18][C:19](=[O:24])OC(C)=C)[CH2:6][N:7]([CH3:17])[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9].[Cl:27][C:28]1[CH:29]=[C:30]([C@@H:34]([C@@H:43]2[CH2:48][CH2:47][CH2:46][NH:45][CH2:44]2)[O:35][CH2:36][CH2:37][NH:38][C:39](=[O:42])[O:40][CH3:41])[CH:31]=[CH:32][CH:33]=1>C1COCC1>[Cl:27][C:28]1[CH:29]=[C:30]([C@@H:34]([C@@H:43]2[CH2:48][CH2:47][CH2:46][N:45]([C:19](=[O:24])[NH:18][C@@H:5]([CH2:4][CH2:3][C:2]([CH3:1])([CH3:25])[CH3:26])[CH2:6][N:7]([CH3:17])[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])=[O:9])[CH2:44]2)[O:35][CH2:36][CH2:37][NH:38][C:39](=[O:42])[O:40][CH3:41])[CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 59201306(S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamateHCID 59598478Carbamic acid,N-[2-[(R)-(3-chlorophenyl)(3R)-3-piperidinylmethoxy]ethyl]-,methyl ester

Product 1

HCID 68709121methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The resulting (S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamate was dissolved in THF (5 mL) and methyl 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate (40 mg, 0.1227 mmol, 1.1 equiv) added and the mixture heated to 50° C. overnight. After completion of the reaction, the solution was washed with 0.5 M HCl, brine, then dried over Na2SO4, filtered, and evaporated to afford crude methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate which was taken directly to the next step.

Workup

  1. customAfter completion of the reaction
  2. washthe solution was washed with 0.5 M HCl, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2933a49e90114b7e86ecccb74188a313
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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