Methylamine → 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-1-(3-chlorophenyl)-1-(2-(methylamino)-2-oxoethoxy)ethyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate

HRID 451915Notes

Reaction equation

HRID 451915 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:45])[NH:24][C@H:25]([CH2:33][N:34]([CH3:44])[C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])=[O:36])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:18]2)([O:10][CH2:11][C:12]([O:14]CC)=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:46][NH2:47]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([NH:24][C@@H:25]([CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:33][N:34]([CH3:44])[C:35](=[O:36])[O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:42])[CH3:43])=[O:45])[CH2:18]2)([O:10][CH2:11][C:12]([NH:47][CH3:46])=[O:14])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68715559ethyl 2-((R)-1-(3-chlorophenyl)-1-((R)-1-((S)-1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)ethoxy)acetate

Product 1

HCID 866394592-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-1-(3-chlorophenyl)-1-(2-(methylamino)-2-oxoethoxy)ethyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-((R)-1-(3-chlorophenyl)-1-((R)-1-((S)-1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)ethoxy)acetate (0.0185 g) and 33% wt. methylamine in ethyl alcohol (10 mL) was stirred at rt for 3 d. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.0035 g of 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-1-(3-chlorophenyl)-1-(2-(methylamino)-2-oxoethoxy)ethyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate. MS ESI +ve m/z 653 (M+H).

Workup

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-1358bb79783e41fe91adcdcb9466f2c0
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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