Acetamide → Acetamidoglycolic acid

HRID 20189

反応式

HRID 20189 の反応式
[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]

参加物

4

反応物 2

HCID 178AcetamideHCID 15620607Glyoxylic acid, monohydrate

生成物 1

HCID 14212846Acetamidoglycolic acid収率 103.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-91ef1df6c0874810b8d62bfcd9f1b566
出典データセット
uspto-grants-2010_06
特許番号
US07745573B2

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