Ethanolamine → Benzoic acid, 3-(6-amino-3-methyl-2-pyridinyl)-, 1,1-dimethylethyl ester

HRID 242135

반응식

HRID 242135 반응식
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N+:15]=2[O-])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1C=CC=CC=1.CS(OS(C)(=O)=O)(=O)=O.C(CN)O>CC#N.O>[C:1]([O:5][C:6](=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([NH2:22])[N:15]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 584883712-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

생성물 1

HCID 45480517Benzoic acid, 3-(6-amino-3-methyl-2-pyridinyl)-, 1,1-dimethylethyl ester수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매2회

반응 조건

온도
10 °C

실험 절차

A solution of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (1 eq) and pyridine (4 eq) in MeCN (8 vol.) is heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) is added over 50 min via addition funnel maintaining the temperature at less than 75° C. The mixture is stirred for an additional 0.5 hours after complete addition. The mixture is then allowed to cool to ambient. Ethanolamine (10 eq) is added via addition funnel. After stirring for 2 hours, water (6 vol.) is added and the mixture is cooled to 10° C. After stirring for NLT 3 hours, the solid is collected by filtration and washed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol). The solid is dried to constant weight (<1% difference) in a vacuum oven at 50° C. with a slight N2 bleed to afford tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate as a red-yellow solid (53% yield).

후처리

  1. temperaturemaintaining the temperature at less than 75° C
  2. additionafter complete addition
  3. temperatureto cool to ambient
  4. stirringAfter stirring for 2 hours
  5. stirringAfter stirring for NLT 3 hours
  6. filtrationthe solid is collected by filtration
  7. washwashed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol)
  8. dry with materialThe solid is dried to constant weight (<1% difference) in a vacuum oven at 50° C. with a slight N2

출처 및 근거

ORD 기록
ord-7ca89493c8724daca4f6cf6f6b38bb6d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653103B2

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