Hydrochloric Acid → N-(heptan-4-yl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide

HRID 2410616

반응식

HRID 2410616 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:27]=[CH:26][C:20]([CH:21]([OH:25])[C:22]([OH:24])=O)=[CH:19][C:18]=1[O:28][CH3:29].ON1C(=O)CCC1=O.[CH3:38][CH2:39][CH2:40][CH:41]([NH2:45])[CH2:42][CH2:43][CH3:44].C(=O)(O)[O-].[Na+].Cl>O1CCOCC1.O>[CH3:38][CH2:39][CH2:40][CH:41]([NH:45][C:22](=[O:24])[CH:21]([OH:25])[C:20]1[CH:26]=[CH:27][C:17]([OH:16])=[C:18]([O:28][CH3:29])[CH:19]=1)[CH2:42][CH2:43][CH3:44]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 1245Vanillylmandelic AcidHCID 10868DicyclohexylcarbodiimideHCID 386654-HeptanamineHCID 80170N-HydroxysuccinimideHCID 516892Sodium Bicarbonate

생성물 1

HCID 49854208N-(heptan-4-yl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide수율 73.6%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

A solution of dicyclohexyl carbodiimide (DCC) (5.5 g, 26.7 mmol) in 1,4-dioxane (50 ml) was added to a stirred solution of 4-hydroxy-3-methoxymandelic acid (5 g, 25.3 mmol) and N-hydroxysuccinimide (3 g, 26.1 mmol) in 1,4-dioxane (100 ml) at room temperature. The resulting white suspension was stirred at room temperature for 16 hours. Then the reaction mixture was filtered. The filtrate was poured into a stirred solution of 4-heptylamine in water (20 ml) and sodium bicarbonate (2.5 g, 20 mmol) was added. The resulting solution was heated to 50° C. and stirred at this temperature for 1.5 hour. The cooled solution was acidified to pH<2 using aq. HCl 5% solution and extracted three times with ethyl acetate (100 ml). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the filtrate concentrated by evaporation under reduced pressure. The residue was purified by crystallization from ethyl acetate/heptane to yield the title product (5.5 g, 73.6%) as white crystals.

후처리

  1. filtrationThen the reaction mixture was filtered
  2. additionwas added
  3. temperatureThe resulting solution was heated to 50° C.
  4. stirringstirred at this temperature for 1.5 hour
  5. extractionextracted three times with ethyl acetate (100 ml)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated by evaporation under reduced pressure
  10. customThe residue was purified by crystallization from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-23bcf3ef293b4ed48b494c2058a26181
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816102B2

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