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

HRID 1697455노트

반응식

HRID 1697455 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d7c2fc7dd43a4f0a9cbda37a77f43de0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163901B2

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