Lithium hydroxide, monohydrate → 3-Bromo-5-[(dimethylamino)methyl]benzoic acid

HRID 1617399노트

반응식

HRID 1617399 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([OH:7])=[O:6]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

생성물 1

HCID 584313873-Bromo-5-[(dimethylamino)methyl]benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 3-bromo-5-[(dimethylamino)methyl]benzoate (0.30 g, 1.1 mmol, from Step A) was dissolved in tetrahydrofuran (20 mL) and lithium hydroxide monohydrate (0.555 g, 13.2 mmol) in water (6 mL) was added. After stirring for 3 hours, the mixture was rotovapped to remove THF and reduce the volume of water. The mixture was diluted with an equivalent volume of acetonitrile and filtered. The product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Solvent was removed from fractions containing desired product by rotary evaporation to afford a white solid. Yield: 0.26 g (91%); LC-MS: 258.0, 260.0 (M+H)+. 1H NMR (300 MHz, DMSO-d6): δ 7.86 (dd, 1H), 7.76 (dd, 1H), 7.43 (dd, 1H), 3.38 (s, 2H), 2.14 (s, 6H).

후처리

  1. customto remove THF
  2. additionThe mixture was diluted with an equivalent volume of acetonitrile
  3. filtrationfiltered
  4. customThe product was purified via preparative HPLC-MS (C18
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  6. customSolvent was removed from fractions
  7. additioncontaining desired product
  8. customby rotary evaporation
  9. customto afford a white solid

출처 및 근거

ORD 기록
ord-c3d6e8d697464cc888a7884b38cb622b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765734B2

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