Ethyl Acetate → HCID 59615978, 화합물

HRID 1950754노트

반응식

HRID 1950754 반응식
[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]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 59615929HCID 59615929, 화합물

생성물 1

HCID 59615978HCID 59615978, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-29d80cea1cc04c69bbd7e3f5673f0566
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404678B2

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