Ethyl Acetate → HCID 59615978、化合物

HRID 1950754ノート

反応式

HRID 1950754 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([CH2:21][OH:22])[CH:20]=1)[O:6][CH2:7][CH2:8][N:9]([CH3:17])[C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14].[CH3:23][Si](C=[N+]=[N-])(C)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH3:23][O:14][C:13](=[O:15])[CH2:12][CH2:11][C:10]([N:9]([CH2:8][CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=1)[CH3:17])=[O:16]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 59615929HCID 59615929、化合物

生成物 1

HCID 59615978HCID 59615978、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

To a cooled (0° C.) solution of N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid (225 mg) in methanol (1 mL), was added (trimethylsilyl)diazomethane 2M in hexanes (840 μL) until persistence of the yellow colour. After 40 min, ethyl acetate (5 mL) and acetic acid (50 μL) were added, then, one minute later, a saturated aqueous solution of sodium hydrogen carbonate until pH=7. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm), using gradient elution with a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B) to give N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid methyl ester (103 mg). LC/MS (Method A3): ES: m/z 348 (M+Na)+; m/z 326 (M+H)+ m/z 308 (M−H2O+H)+; RT=0.43 min

後処理

  1. customone minute
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a residue
  6. customThe residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm)
  7. washelution
  8. additionwith a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B)

出典と根拠

ORDレコード
ord-29d80cea1cc04c69bbd7e3f5673f0566
出典データセット
uspto-grants-2013_03
特許番号
US08404678B2

反応ノート

読み込み中…