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

HRID 76981

反応式

HRID 76981 の反応式
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

参加物

9

反応物 5

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

生成物 1

HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochloride収率 63%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-99cdd32759ab4cd194d408358df71df5
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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