Hydrochloric Acid → HCID 58534191, compound

HRID 2174259Notes

Reaction equation

HRID 2174259 reaction equation
Cl[C:2]([O:4][CH:5]1[CH:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][CH2:8][CH:7]([CH3:14])[CH2:6]1)=[O:3].[N:15]1C=CC=[CH:17][CH:16]=1.C(N)C.Cl>C1(C)C=CC=CC=1.O>[CH:11]([C@@H:10]1[CH2:9][CH2:8][C@@H:7]([CH3:14])[CH2:6][C@H:5]1[O:4][C:2](=[O:3])[NH:15][CH2:16][CH3:17])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6341EthylamineHCID 151928Menthyl chloroformate

Product 1

HCID 58534191HCID 58534191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

58.7 g of menthyl chloroformate (80% in toluene) were added to a mixture of 16.6 g of pyridine and 150 mL ethylamine (2M solution in THF) in 100 mL toluene at 0° C. over a period of 30 minutes. After stirring for 12 hours at room temperature, 100 mL of 2M HCl and subsequently 50 mL water were added, the phases separated and the water phase discarded. After washing with saturated NaHCO3-solution and water the organic phase was dried and evaporated to yield 47.1 g of crude product which was recrystallized from 82.4 g n-heptane to give 24.4 g of the analytically pure product as white crystals.

Workup

  1. customthe phases separated
  2. washAfter washing with saturated NaHCO3-solution and water the organic phase
  3. customwas dried
  4. customevaporated
  5. customto yield 47.1 g of crude product which
  6. customwas recrystallized from 82.4 g n-heptane
  7. customto give 24.4 g of the analytically pure product as white crystals

Sources & evidence

ORD record
ord-9297637341464b5db4e0d3ba3082ff1c
Source dataset
uspto-grants-2015_06
Patent number
US09060949B2

Reaction notes

Loading…