4-Methylmorpholine → {[4-Phenoxy-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

HRID 37746ノート

反応式

HRID 37746 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][C:19](O)=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[NH2:33][OH:34].Cl.[OH-].[K+]>C1COCC1.CO>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][C:19](=[O:20])[NH:33][OH:34])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 66916737HCID 66916737、化合物

生成物 1

HCID 16126723{[4-Phenoxy-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Compound 5a (711 mg, 1.95 mmol) was dissolved in dry THF (5 mL). ECF (160 μL, 1.95 mmol), and NMM (180 μL, 1.95 mmol) were added and this mixture was stirred for 40 min at 0° C. NH2OH.HCl (136 mg, 1.95 mmol) and KOH (109 mg, 1.95 mmol) were dissolved in dry MeOH (5 mL) and stirred at 0° C. for 30 min. The solids were filtered off, and the THF solution was added dropwise to the methanol filtrate and stirred for 2 h at 0° C. The reaction mixture was filtered, the solvent evaporated, and the residue dissolved in H2O (25 mL). After adjusting the pH to 1-2, the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were dried over MgSO4, evaporated in vacuo, and co-evaporated with EtOAc (3×3 mL) to yield the pure product as light-pink solid. Yield: 565 mg, 1.10 mmol, 56%. 1H-NMR (DMSO-d6): δ 7.87 (d, 2H, 2JHH=9.0 Hz, ArH), 7.42 (d, 2H, 2JHH=9.0 Hz, ArH), 7.35 (s, 2H, ArH), 6.98 (d, 1H, 3JHH=9.0 Hz, ArH), 6.90 (d, 2H, 3JHH=9.0 Hz, ArH), 4.07 (s, 2H, 2×CH2CO2H), 3.85 (s, 2H, 2×CH2CONHOH). ESI-MS calcd for C16H16N2O7S 380.07 [M-H]−, obsd 381.1.

後処理

  1. stirringstirred at 0° C. for 30 min
  2. filtrationThe solids were filtered off
  3. additionthe THF solution was added dropwise to the methanol filtrate
  4. stirringstirred for 2 h at 0° C
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent evaporated
  7. dissolutionthe residue dissolved in H2O (25 mL)
  8. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-11b5b26d35a746f090cd9c6d3d12dc1b
出典データセット
uspto-grants-2013_09
特許番号
US08524194B2

反応ノート

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