Sulfuric Acid → O-Methyl-L-tyrosine methyl ester

HRID 333409ノート

反応式

HRID 333409 の反応式
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.S(=O)(=O)(O)O.[OH-].[Na+].[C:29](=O)([O-])O.[Na+]>CO>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:29])=[O:11]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 2762280Boc-O-methyl-L-tyrosine

生成物 1

HCID 10856719O-Methyl-L-tyrosine methyl ester収率 90%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To 10 g (33.8 mmol) of (S)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid are added 75 mL of methanol and then 10 mL of sulfuric acid dropwise over 30 minutes. After 30 hours, the reaction medium is basified to pH 8-9 by adding aqueous 10N sodium hydroxide solution followed by saturated sodium hydrogen carbonate solution. The organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate and then filtered, and the solvents are evaporated off. 6.36 g of methyl (S)-2-amino-3-(4-methoxyphenyl)propionate in the form of a brown oil are obtained in a yield of 90%.

後処理

  1. extractionThe organic products are extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvents are evaporated off

出典と根拠

ORDレコード
ord-9ef3a30e3ce74f41bacb55991e91c5f9
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

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