Sodium Hydroxide → HCID 44242581, 화합물

HRID 1775960노트

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HRID 1775960 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14]CC)=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 57930381HCID 57930381, 화합물

생성물 1

HCID 44242581HCID 44242581, 화합물수율 21.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

Ethyl 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate (0.3 g, 2.9 mmol) in THF (10 mL) was added to a solution of sodium hydroxide (0.177 g, 2.9 mmol) in water (3 mL) and heated at 75° C. for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed; water (10 mL) was added to the residue and the aqueous layer was washed with ethyl acetate (2×10 mL). The pH of aqueous layer was adjusted to 2-3, and the aqueous layer was washed with ethyl acetate. The aqueous layer was evaporated, the residue was extracted with methanol, filtered, the filtrate was concentrated under reduced pressure to yield 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid (175 mg). 1H NMR (CD3OD): 7.50 (s, 1H) 7.30 (d, 1H), 7.10 (d, 1H), 5.1 (d, 1H), 5.0 (d, 1H), 4.4 (s, 2H), 4.2 (m, 1H), 4.0 (m, 1H), 3.4 (s, 3H), 3.2 (m, 2H).

후처리

  1. customAfter completion of the reaction
  2. customthe solvent was removed
  3. additionwater (10 mL) was added to the residue
  4. washthe aqueous layer was washed with ethyl acetate (2×10 mL)
  5. washthe aqueous layer was washed with ethyl acetate
  6. customThe aqueous layer was evaporated
  7. extractionthe residue was extracted with methanol
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d66e3aa2fcb040de9d3fcd39aeed533b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260429B2

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