Tetrahydrofuran → N-Boc-4-chloro-3-fluoro-D-phenylalanine

HRID 1675832노트

반응식

HRID 1675832 반응식
O[Li].O.[C:4]([O:8][C:9]([NH:11][C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=1)[C:13]([O:15]C)=[O:14])=[O:10])([CH3:7])([CH3:6])[CH3:5].C1COCC1>O>[C:4]([O:8][C:9]([NH:11][C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=1)[C:13]([OH:15])=[O:14])=[O:10])([CH3:7])([CH3:5])[CH3:6]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67338942(R)-methyl 2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoate

생성물 1

HCID 67340403N-Boc-4-chloro-3-fluoro-D-phenylalanine수율 83.1%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

LiOH—H2O (0.6246 g, 14.88 mmol) was added to a solution of (R)-methyl 2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoate (1.646 g, 4.961 mmol) in 1:1 THF:H2O (26 mL). The reaction mixture was stirred at room temperature for 2 hours, after which it was diluted with H2O and washed with EtOAc. The aqueous layer was then acidified with solid KHSO4 and extracted with DCM. The combined extracts were dried (Na2SO4), filtered, concentrated, and then re-concentrated from DCM/hexanes to give (R)-2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoic acid (1.31 g, 83.10% yield) as a white powder. LCMS (APCI−) m/z 316 [M−H]−.

후처리

  1. washwashed with EtOAc
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationre-concentrated from DCM/hexanes

출처 및 근거

ORD 기록
ord-16eda8ef798c4b458c04f97c2d7e42e1
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003651B2

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