Glyoxylic Acid → HCID 10704686, compound

HRID 906468Notes

Reaction equation

HRID 906468 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[C:6]1([C@H:12]([NH:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[C:6]1([C@H:12]([N:14]2[CH2:15][CH2:16][C@@H:17]3[CH2:18][C@H:2]2[C:1](=[O:4])[O:5]3)[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 760Glyoxylic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 10487489HCID 10487489, compound

Product 1

HCID 10704686HCID 10704686, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

Glyoxylic acid (7.43 mL) was added dropwise to a solution of (R)—N-(1-phenylethyl)but-3-en-1-amine (7.80 g) in tetrahydrofuran (30 mL) at 60° C. over a period of 1.5 h. The reaction was heated at 60° C. for a further 7 h. Water (30 mL) and brine (30 mL) were added and the pH adjusted with 2M NaOH solution to pH 9. The aqueous was extracted with ethyl acetate (3×50 mL), the organics combined, washed with saturated aqueous NaHCO3 solution, water, brine, dried (MgSO4), filtered and evaporated to afford an orange oil (9.5 g). Purification (SiO2 chromatography using elution gradient 25% ethyl acetate in isohexane) afforded the subtitle product (3.10 g) as an orange oil.

Workup

  1. extractionThe aqueous was extracted with ethyl acetate (3×50 mL)
  2. washwashed with saturated aqueous NaHCO3 solution, water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0526a190ed944c8caf9c8e5ccd9d83a8
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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