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

HRID 1358596

반응식

HRID 1358596 반응식
[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]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 7019130Boc-Tyr-OMe

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-50bfa75144c34bf7995b8cf121ecb483
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596752B1

연결된 노트

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