Lithium Hydroxide → HCID 57457166, 화합물

HRID 2114399노트

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HRID 2114399 반응식
[CH3:1][O:2][C:3]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:6]2[N:7]([CH2:12][C:13]([O:15]CC)=[O:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1.[Li+].[OH-].CC#N.O.FC(F)(F)C(O)=O>O1CCCC1.O>[CH3:1][O:2][C:3]1[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:6]2[N:7]([CH2:12][C:13]([OH:15])=[O:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

참가 물질

7

반응물 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 57437814Ethyl[7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate

생성물 1

HCID 57457166HCID 57457166, 화합물수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl [7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate (0.36 g, 1.1 mmol) was dissolved in 4 mL of tetrahydrofuran and treated with a solution of LiOH (0.028 g, 1.2 mmol) dissolved in 0.5 mL of water. The reaction was stirred vigorously at room temperature for 18 hours before it was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=1.62 min and m/e 306 [M+1]+. The solvent was removed by rotary evaporation and the residue was then dissolved in 50 mL of ethyl acetate. The organic layer was washed with a 10% hydrochloric acid solution (3×10 mL) and the organic phase was then dried over Na2SO4, filtered and concentrated to give [7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetic acid (0.31 g, 1.0 mmol, 91%) as an off-white amorphous solid. MS (ES) m/e 306 [M+H]+.

후처리

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was then dissolved in 50 mL of ethyl acetate
  3. washThe organic layer was washed with a 10% hydrochloric acid solution (3×10 mL)
  4. dry with materialthe organic phase was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-132353bbd3054583aab3e56df6c1443a
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432258B2

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