Hydrochloric Acid → 1-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

HRID 1942711노트

반응식

HRID 1942711 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>O1CCCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH2:23][N:24]4[CH2:25][CH:26]([C:28]([OH:30])=[O:29])[CH2:27]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58494145HCID 58494145, 화합물

생성물 1

HCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid수율 105.4%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylate (D13) (30.3 g, 62.3 mmol) in Tetrahydrofuran (THF) (200 mL), Ethanol (150 mL) and Water (60 mL) was added sodium hydroxide (4.99 g, 125 mmol). The reaction mixture was stirred at room temperature overnight. Then pH of the reaction mixture was adjusted with 6 N HCl until pH ˜2.0. White solid was precipitated. The organic solvent was removed in by rotary evaporator. The solid was collected through filtration. The solid was washed water (150 mL×3) and dried in vacuo to afford 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3 azetidinecarboxylic acid (31 g), which was used for the following procedure without further purification.

후처리

  1. customWhite solid was precipitated
  2. customThe organic solvent was removed in by rotary evaporator
  3. filtrationThe solid was collected through filtration
  4. washThe solid was washed water (150 mL×3)
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-9929a74fd5ce47bdb220a735333595b2
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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