Hydrochloric Acid → 5-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid

HRID 453304

반응식

HRID 453304 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([O:21]CC)=[O:20].[Li+].[OH-].Cl>CO.C1COCC1.O.[Cl-].[Na+].O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([OH:21])=[O:20]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67434696Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate

생성물 1

HCID 585519085-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid수율 75%

시약·촉매·용매 3

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate (2.6 g, 7.9 mmol) was dissolved in MeOH/THF (1:1, 60 mL) and a solution of LiOH (378 mg, 15.7 mmol) in H2O (15 mL) was added. The reaction was stirred for ˜5 h and the pH adjusted to ˜3 by the addition of 3N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated. The crude product was crystallized from EtOAc to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (1.8 g, 75% yield).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was crystallized from EtOAc

출처 및 근거

ORD 기록
ord-d2636f9ce455440e9de42ac466ea02c2
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492401B2

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