(2S)-tert-butyl 1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate → (S)-2-(trimethylsilyl)ethyl 2-amino-1-cyclohexylpentan-3-yl(methyl)carbamate

HRID 451772Notes

Reaction equation

HRID 451772 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:23]C(=O)OC(C)(C)C)[CH:9]([N:12]([CH3:22])[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOCC.CCO>[NH2:23][C@H:8]([CH:9]([N:12]([CH3:22])[C:13](=[O:14])[O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[CH2:10][CH3:11])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

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

Product 1

HCID 68713179(S)-2-(trimethylsilyl)ethyl 2-amino-1-cyclohexylpentan-3-yl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The (2S)-tert-butyl 1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate (137 mg, 0.14 mmol) was dissolved in Et2O (5 mL), anhydrous TSA (24 mg, 0.14 mmol) dissolved in EtOH was added. The solvent was removed in vacuo using a hot bath at 60° C. for 30 min to give (S)-2-(trimethylsilyl)ethyl 2-amino-1-cyclohexylpentan-3-yl(methyl)carbamate. MS ESI +ve m/z 343 (M+H).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customat 60° C.
  4. customfor 30 min

Sources & evidence

ORD record
ord-7413b34eb1dd45dda463514a57a20ad1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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