Acetone → Methyl 2-[2-Hydroxy-3-[N-[2-[N-(4-methylphenylsulfonyl)amino]ethyl]amino]propoxy]benzoate Oxalate

HRID 1164986

반응식

HRID 1164986 반응식
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[O:15]1[CH2:29][CH:16]1[CH2:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].CC(C)=O>CO>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].[OH:15][CH:16]([CH2:29][NH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 971Oxalic AcidHCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoateHCID 301318N-(2-Aminoethyl)-4-methylbenzenesulfonamide

생성물 1

HCID 13732868Methyl 2-[2-Hydroxy-3-[N-[2-[N-(4-methylphenylsulfonyl)amino]ethyl]amino]propoxy]benzoate Oxalate

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of 2.15 g of N-(2-aminoethyl)-p-toluenesulfonamide (0.1 mole) and 2.08 g of methyl 2-(2,3-epoxypropoxy)benzoate (0.01 mole) in 100 ml of methanol was stored at 25° C. for 4 hours. The methanol was then removed under reduced pressure, leaving an oil (NMR indicated only mono-alkylated product). The oil was then dissolved in 50 ml of methanol and an equimolar quantity of oxalic acid was added to the solution. 50 Ml of acetone was added, and the product crystallized upon refrigeration. The product was recrystallized from acetone/methanol (1:1) to yield 1.4 g of product which had a melting point of 165°-166° C. The elemental analysis (CHN) and NMR spectrum were consistent with the assigned structure.

후처리

  1. customThe methanol was then removed under reduced pressure
  2. customleaving an oil (NMR
  3. customthe product crystallized upon refrigeration
  4. customThe product was recrystallized from acetone/methanol (1:1)

출처 및 근거

ORD 기록
ord-f997e7ee0d014e91a957e1f7bb5f7009
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04906661

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