Hydrochloric Acid → 6-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid

HRID 1697455ノート

反応式

HRID 1697455 の反応式
C([O:3][C:4]([CH:6]1[CH2:11][NH:10][C:9]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:8]=2[O:7]1)=[O:5])C.[OH-].[Na+].ClC(OCC1C=CC=CC=1)=O.Cl>O1CCOCC1.O>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:14]=[CH:15][C:8]2[O:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][NH:10][C:9]=2[CH:12]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 11747775ethyl 6-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

生成物 1

HCID 203952756-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid収率 66.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

6-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (500 mg, 2 mmol) was dissolved in 1,4-dioxane (20 mL). Sodium hydroxide (109 mg, 2.7 mmol) was added, followed by benzyl chloroformate (311 μL, 2.2 mmol), and the reaction stirred overnight at room temperature. The reaction mixture was acidified with 2N HCl and diluted with water (20 mL), then extracted with EtOAc (3×30 mL). The combined organics were washed with brine (2×40 mL), dried (MgSO4), filtered and concentrated. Trituration using DCM/hexanes gave the title compound (330 mg, 10%) as a pale brown solid. m/z=245.7 (M−1), r.t.=2.78 mins. 1H NMR (400 MHz; CDCl3) δ 7.01 (2H, s), 6.86 (1H, s), 4.94 (1H, t), 3.66 (2H, dd).

後処理

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organics were washed with brine (2×40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d7c2fc7dd43a4f0a9cbda37a77f43de0
出典データセット
uspto-grants-2012_04
特許番号
US08163901B2

反応ノート

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