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

HRID 625034ノート

反応式

HRID 625034 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-23aa604ca2c44aa78c28521bfb429530
出典データセット
uspto-grants-2016_04
特許番号
US09303040B2

反応ノート

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