Hydrochloric Acid → Phenyl-o-methylphenylamino-acetic acid hydrochloride

HRID 76981

반응식

HRID 76981 반응식
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.CCN(C(C)C)C(C)C.O.[OH-].[Li+].[ClH:34]>C(#N)C.O1CCOCC1.O>[ClH:34].[C:8]1([CH:2]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:3]([OH:5])=[O:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 7242O-ToluidineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetateHCID 168937Lithium hydroxide, monohydrate

생성물 1

HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochloride수율 63%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Ethyl 2-bromo-2-phenylacetate (0.28 mL, 1.64 mmol), ortho-toluidine (0.26 mL, 2.47 mmol) and DIPEA (0.43 mL, 2.47 mmol) are dissolved in acetonitrile (5 mL) and stirred under MW irradiation at 100° C. for 1 hour (Conversion complete by UPLC/MS-UV). Lithium hydroxide hydrate (207 mg, 4.94 mmol) and water (3 mL) are added and the mixture is stirred at RT for 16 hours. 4M HCl in dioxane is added until pH is about 1, then the solvents are evaporated, the residue is suspended in water, sonicated, cooled at 0° C. and the resulting solid is recovered by filtration and dried under vacuum to get intermediate I86 as a off-white solid (290 mg, 63% yield).

후처리

  1. stirringthe mixture is stirred at RT for 16 hours
  2. customthe solvents are evaporated
  3. customsonicated
  4. temperaturecooled at 0° C.
  5. filtrationthe resulting solid is recovered by filtration
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-99cdd32759ab4cd194d408358df71df5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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