Oxalic Acid → 6-(Pyridine-3-sulfonylamino)hexanoic acid hydroxyamide oxalate

HRID 226189

반응식

HRID 226189 반응식
C[O-].[Na+].Cl.[NH2:5][OH:6].[Na+].[Cl-].C[O:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>CO>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[OH:6][NH:5][C:11](=[O:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19]

참가 물질

7

반응물 5

HCID 971Oxalic AcidHCID 5234Sodium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 207804896-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester

생성물 1

HCID 865919036-(Pyridine-3-sulfonylamino)hexanoic acid hydroxyamide oxalate수율 44%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of sodium methylate (12 mmol) in methanol (10 ml) was added to a solution of hydroxylamine hydrochloride (0.56 g, 8 mmol) in methanol (16 ml). The mixture was stirred for 10 min, and NaCl was filtered off 6-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester (93c) (0.58 g, 2 mmol) was added to the filtrate and the mixture was left to stand overnight at ambient temperature. The precipitate was filtered off, dissolved in water (20 ml) and oxalic acid (0.36 g, 4 mmol) was added to the solution. Water was removed under reduced pressure and the product was crystallised from methanol. The title compound (0.33 g, 44%) was obtained as white solid. M.p. 132-134° C. 1H NMR δH. (90 MHz, DMSO-d6) δ: 0.78-1.49 (6H, m, CH2), 1.83 (2H, t, J=6.5 Hz, CH2); 2.76 (2H, t, J=6.5 Hz, CH2N); 7.54 (1H, dd, J=5.0 Hz, J=8.2 Hz, C5HN); 8.12 (1H, dt, J=2.0 Hz, J=8.2 Hz, C5HN); 8.61 (1H, dd, J=2.0 Hz, J=5.0 Hz, C5HN); 8.81 (1H, d, J=2.0 Hz, C5HN). HPLC analysis on Symmetry C18 column: impurities <1% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 5: 95; detector UV 254 nm; sample concentration 1.0 mg/ml). Anal. Calcd for C11H17N3O4S*(COCH)2: C 41.38, H 5.07, N 11.13. Found: C 41.53, H 5.10, N 19.83.

후처리

  1. additionwas added to the filtrate
  2. waitthe mixture was left
  3. waitto stand overnight at ambient temperature
  4. filtrationThe precipitate was filtered off
  5. dissolutiondissolved in water (20 ml)
  6. customWater was removed under reduced pressure
  7. customthe product was crystallised from methanol

출처 및 근거

ORD 기록
ord-f8b0131305ac413bb702d741917e569a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557140B2

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