Lithium Hydroxide → 3-Chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylic acid

HRID 1874965노트

반응식

HRID 1874965 반응식
[Li+].[OH-].[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[NH:6][C:5]=1[C:15]([O:17]C)=[O:16]>C1COCC1.CO>[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[NH:6][C:5]=1[C:15]([OH:17])=[O:16]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 68487232Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

생성물 1

HCID 684835273-Chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylic acid수율 54.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

LiOH (2 mL, 2 mmol) was added to a solution of methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate (0.082 g, 0.33 mmol) in THF (2 mL) and methanol (2 mL). The solution was stirred at RT overnight. The solvent was evaporated and the residue partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4, filtered and evaporated to afford very little solid. The aqueous layer was evaporated to a residue and the salts extracted with methanol. The methanol was evaporated to afford the title compound (0.042 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.16 (br. s., 1H), 8.40 (t, 1H), 6.61-7.10 (m, 1H), 3.45 (t, 2H), 3.26 (q, 2H).

후처리

  1. customThe solvent was evaporated
  2. customthe residue partitioned between EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford very little solid
  8. customThe aqueous layer was evaporated to a residue
  9. extractionthe salts extracted with methanol
  10. customThe methanol was evaporated

출처 및 근거

ORD 기록
ord-d75fd0152b0f4dcf8f4f7d6c5770480b
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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