Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 10988904, compound

HRID 451762

Reaction equation

HRID 451762 reaction equation
C[Si](C)(C)CCOC([NH:8][CH2:9][C@@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=O.[N+](CC)(CC)(CC)CC.[F-]>CC#N>[NH2:8][CH2:9][C@@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 59382914HCID 59382914, compound

Product 1

HCID 10988904HCID 10988904, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (S)-tert-butyl 1-(2-(trimethylsilyl)ethoxycarbonylamino)-3-cyclohexylpropan-2-ylcarbamate (6.55 g, 15.4 mmol) in MeCN (100 mL) was added Et4NF (7.5 g, 50 mmol). The mixture was stirred overnight at rt and at 60° C. for 7 h. The mixture was concentrated and the oily residue was taken up in EtOAc (175 mL). The mixture was washed with water (2×50 mL) and brine (50 mL) and dried over Na2SO4. Removal of the solvent afforded (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate (3.39 g, 80%) as a syrup.

Workup

  1. concentrationThe mixture was concentrated
  2. washThe mixture was washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-18651ba18c464d10a01bba32b765863c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

Loading…