Nitric Acid → (S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

HRID 1018701

反応式

HRID 1018701 の反応式
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[N+:22]([O-])([OH:24])=[O:23]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 7019130Boc-Tyr-OMe

生成物 1

HCID 15518593(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-(tert-butoxycarbonyl)-L-tyrosine methyl ester (5.64 g) in THF (10 ml) was added NH4NO3 (3 g) and concentrated HNO3 (3 ml). After 30 sec., the reaction mixture turned to dark red with reflux occurring. The reaction mixture was quenched with solid NaHCO3 and H2O, and extracted with AcOEt. The extract was dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt) to give N-(tert-butoxycarbonyl)-3-nitro-L-tyrosine methyl ester (3.42 g). The obtained compound was treated in a similar manner as described in R. Example 4 to give 3-Nitro-L-tyrosine methyl ester, hydrochloride salt.

後処理

  1. temperaturewith reflux
  2. customThe reaction mixture was quenched with solid NaHCO3 and H2O
  3. extractionextracted with AcOEt
  4. dry with materialThe extract was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluent; Hexane→1:1, Hexane/AcOEt)

出典と根拠

ORDレコード
ord-115ac3775c2c4af696b5770917a14861
出典データセット
uspto-grants-2002_11
特許番号
US06482849B1

関連ノート

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