Acetamide → Acetamidoglycolic acid

HRID 1645217Notes

Reaction equation

HRID 1645217 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].O.[C:6]([OH:10])(=[O:9])[CH:7]=[O:8]>CC(C)=O>[C:1]([NH:4][CH:7]([OH:8])[C:6]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 178AcetamideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 14212846Acetamidoglycolic acidYield 103.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The titled compound 42 was prepared according to a procedure described by Williams et al.195 A solution of acetamide 34 (6.10 g, 0.10 mol) and glyoxylic acid monohydrate 41 (10.60 g, 0.14 mol) in anhydrous acetone (150 mL) was heated at reflux for 18 h. The reaction mixture was evaporated under reduced pressure to afford the desired product 42 as a viscous yellow oil (13.75 g, 100%). Spectroscopic data indicated the crude product 42 did not require purification and was used directly in the subsequent reaction (Section 7.9.2). νmax (neat): 3317bs, 2974w, 1732s, 1668s, 1538s, 1379m, 1234w, 1112w, 1048m, 880m cm−1. 1H n.m.r. (300 MHz, D6-DMSO): δ 1.84 (s, 3H, CH3CO), 5.39 (d, J=8.7 Hz, 1H, H2), (8.65, bd, J=8.4 Hz, 1H, NH), two exchangeable protons (OH) not observed. 13C n.m.r. (75 MHz, D6-DMSO): δ 22.5 (CH3CO), 70.9 (C2), 169.4 (CONH), 171.5 (C1). Mass Spectrum (ESI+, MeOH): m/z 134.2 (M+H)+, C4H8NO4 requires 134.1. Spectroscopic data were in agreement with those reported in the literature.195

Workup

  1. customThe titled compound 42 was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 18 h
  4. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21ec2814393d4ffc9eceb832fe543c37
Source dataset
uspto-grants-2012_02
Patent number
US08124726B2

Reaction notes

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