Carbon Dioxide → 4-Morpholinotetrolic acid

HRID 1068974Notes

Reaction equation

HRID 1068974 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[C:6]([NH2:13])(=O)[CH:7]=CC=CC.[C:14](=[O:16])=[O:15].[OH2:17].CCCC[CH2:22][CH3:23]>O1CCCC1.CO>[N:13]1([CH2:3][C:2]#[C:1][C:14]([OH:16])=[O:15])[CH2:6][CH2:7][O:17][CH2:22][CH2:23]1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 962WaterHCID 8058HexaneHCID 265085HCID 265085, compoundHCID 178418339Butyllithium

Product 1

HCID 5419084-Morpholinotetrolic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium in hexane (51 mL, 2.5M in n-hexane) was slowly added to hexa-2,4-dienoic acid amide (16 g, 128 mmol) in 200 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 13 g of 4-morpholin-4-yl-but-2-ynoic acid: mass spectrum (m/e):M−H 168.

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-8b0c47f3dd2844d1b28b84dbae898392
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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