Lithium hydroxide, monohydrate → 3-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoic acid

HRID 1426139노트

반응식

HRID 1426139 반응식
[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[N:20]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[N:20]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 59225684Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate

생성물 1

HCID 592256533-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoic acid수율 93.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate (2.00 g, 5.41 mmol) was dissolved in THF (5 mL), and a solution of lithium hydroxide monohydrate (469 mg, 11.18 mmol) in water (1 mL) was added at room temperature. The resulting mixture was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo to remove most of the THF, and the resulting aqueous phase was acidified to pH 3 with 2 M aqueous HCl. The resulting cloudy mixture was extracted with CH2Cl2 (3×10 mL), and the combined organic phases were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to a white solid. The solid was further dried under high vacuum overnight to provide the title compound as an off-white powder (1.79 g, 5.04 mmol, 93% yield). 1H NMR (DMSO-d6) δ 2.60 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.2 Hz, 2H), 5.26 (s, 2H), 6.62 (s, 1H), 6.89 (dd, J=7.8, 5.1 Hz, 1H), 7.35 (m, 4H), 7.57 (s, 1H), 7.58 (m, 1H), 7.86 (dd, J=1.5, 5 Hz, 1H), 9.96 (br s, 1H), 12.14 (br s, 1H); Mass spectrum (apci) m/z 354.0 (M−H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove most of the THF
  3. extractionThe resulting cloudy mixture was extracted with CH2Cl2 (3×10 mL)
  4. washthe combined organic phases were washed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a white solid
  8. customThe solid was further dried under high vacuum overnight

출처 및 근거

ORD 기록
ord-026534000c1c48d2ba19a3f288c3eac7
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

반응 노트

불러오는 중…