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

HRID 82356ノート

反応式

HRID 82356 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-6af4e6df28e04c5d97636a3ae77201e8
出典データセット
uspto-grants-2014_09
特許番号
US08846681B2

反応ノート

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