2,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate → (2S)-tert-butyl 1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate

HRID 451771Notes

Reaction equation

HRID 451771 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]([NH:12][CH3:13])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]([O:31]N1C(=O)CCC1=O)([O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=O>C1COCC1>[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]([N:12]([CH3:13])[C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])=[O:31])[CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59201714(S)-tert-butyl 1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamate

Product 1

HCID 68713330(2S)-tert-butyl 1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (S)-tert-butyl 1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamate in THF (20 mL) was added TeocOSu (398 mg, 1.53 mmol), followed by TEA (0.5 mL). The reaction mixture was stirred for 30 min at rt, and concentrated. The residue was partially purified through chromatography on silica gel to give (2S)-tert-butyl 1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate. MS ESI +ve m/z 465 (M+Na).

Workup

  1. concentrationconcentrated
  2. customThe residue was partially purified through chromatography on silica gel

Sources & evidence

ORD record
ord-a184426d266a4788991b8521d11f5c3e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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