Carbon Dioxide → HCID 11745280, compound

HRID 1068994Notes

Reaction equation

HRID 1068994 reaction equation
C([Li])CCC.[CH:6]([N:9]([CH:13]([CH3:15])[CH3:14])[CH2:10][C:11]#[CH:12])([CH3:8])[CH3:7].[C:16](=[O:18])=[O:17].O>CCCCCC.O1CCCC1.CO>[CH:6]([N:9]([CH:13]([CH3:15])[CH3:14])[CH2:10][C:11]#[C:12][C:16]([OH:18])=[O:17])([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 2343732-Propyn-1-amine, N,N-bis(1-methylethyl)-HCID 178418339Butyllithium

Product 1

HCID 11745280HCID 11745280, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium in hexane (28.8 mL, 2.5 M in n-hexane) was slowly added to diisopropyl-prop-2-ynyl-amine (10.0 g, 72 mmol) in 70 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 hr at −78° C., then dry carbon dioxide was passed through overnight. The resulting solution was poured into water and washed with ethyl acetate. The aqueous layer was evaporated under reduced pressure to give the crude acid. The dry acid was dissolved in methanol, and the insoluble salt was removed via filtration. The filtrate was collected and dried in vacuo to give 11 g of 4-diisopropylamino-but-2-ynoic acid: mass spectrum (m/e): M−H 182.

Workup

  1. washwashed with ethyl acetate
  2. customThe aqueous layer was evaporated under reduced pressure
  3. customto give the crude acid
  4. customthe insoluble salt was removed via filtration
  5. customThe filtrate was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7212e5f2680240f69c0d2f941999072d
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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