Ethyl Acetate → 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]benzoic acid

HRID 548733노트

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HRID 548733 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1)[C:5]([OH:7])=[O:6].F[C:18]1[CH:29]=[CH:28][C:21]2[C:22](=[O:27])[N:23]([CH3:26])[CH2:24][O:25][C:20]=2[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[CH3:16][C@H:12]([O:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([O:1][C:18]2[CH:29]=[CH:28][C:21]3[C:22](=[O:27])[N:23]([CH3:26])[CH2:24][O:25][C:20]=3[CH:19]=2)[CH:10]=1)[C:5]([OH:7])=[O:6])[CH2:13][O:14][CH3:15]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 576631937-Fluoro-3-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-oneHCID 576632243-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoic acid

생성물 1

HCID 576631913-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]benzoic acid수율 80.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
160 °C

실험 절차

A mixture of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (175 mg, 0.77 mmol), 7-fluoro-3-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (141 mg, 0.77 mmol) and potassium carbonate (321 mg, 2.32 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 160° C. for 16 hours then reduced in vacuo and ethyl acetate (50 mL) added. The mixture was washed with water (50 mL), the aqueous layer acidified with 1M citric acid and extracted into ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a brown oil (0.24 g). m/z 453 (M+H)+

후처리

  1. additionadded
  2. washThe mixture was washed with water (50 mL)
  3. extractionextracted into ethyl acetate (2×50 mL)
  4. washThe combined organics were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-7289c0bf0d314bc6a67209bf47df9aed
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943607B2

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