Hydrochloric Acid → 3182-88-5

HRID 378930Notes

Reaction equation

HRID 378930 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.[ClH:20]>C(OCC)C>[ClH:20].[CH2:1]([NH:5][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6558IsobutylamineHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 857809383182-88-5

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of isobutylamine (0.90 mL, 0.0091 mol), bromoacetic acid, ethyl ester (1.0 mL, 0.0090 mol), and triethylamine (1.28 mL, 0.00918 mol) in diethylether (15 mL) was stirred at room temperature for 24 hours. The resulting suspension was filtered off and washed with diethylether. The filtrate and washings were combined and rotary evaporated to an oil. The oil was chromatographed on silica gel (150 g, 230-400 mesh) eluting with dichloromethane-diethylether (19:1, 8×125 mL; 15:1, 7×125 mL; 10:1, 15×125 mL). Fractions containing product were combined and rotary evaporated to give an oil. The oil was dissolved in diethylether, concentrated hydrochloric acid (0.52 mL, 0.0063 mol HCl) was added, and the volatiles were rotary evaporated to give a white solid. The solid was dried in vacuo; yield 1.0 g (59%).

Workup

  1. filtrationThe resulting suspension was filtered off
  2. washwashed with diethylether
  3. customrotary evaporated to an oil
  4. customThe oil was chromatographed on silica gel (150 g, 230-400 mesh)
  5. washeluting with dichloromethane-diethylether (19:1, 8×125 mL; 15:1, 7×125 mL; 10:1, 15×125 mL)
  6. additionFractions containing product
  7. customrotary evaporated
  8. customto give an oil
  9. customthe volatiles were rotary evaporated
  10. customto give a white solid
  11. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-7a8c8f5aa59f466cb29876adc29aeb45
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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