Hydrochloric Acid → ({2-Chloro-5-[5-(3-chlorothiophene-2-yl)-(1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid

HRID 856983노트

반응식

HRID 856983 반응식
C([O:3][C:4](=[O:26])[CH2:5][N:6]([C:8]1[CH:13]=[C:12]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][C:23]=3[Cl:24])[O:16][N:15]=2)[CH:11]=[CH:10][C:9]=1[Cl:25])[CH3:7])C.[OH-].[Na+].Cl>C1COCC1.C(O)C.O>[Cl:25][C:9]1[CH:10]=[CH:11][C:12]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][C:23]=3[Cl:24])[O:16][N:15]=2)=[CH:13][C:8]=1[N:6]([CH2:5][C:4]([OH:26])=[O:3])[CH3:7]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 16222813((2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid ethyl ester

생성물 1

HCID 16222814({2-Chloro-5-[5-(3-chlorothiophene-2-yl)-(1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid수율 44%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a white suspension of ({2-chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid ethyl ester (0.362 g, 0.880 mmol) in an EtOH:H2O solution (4:1, 13.4 mL) was added 1M NaOH (0.033 mL, 0.84 mmol). Additional aliquots of 1M NaOH (1.98 μL, 50.34 mmol), ethanol (8 mL) and THF (10 mL) was added and the mixture was stirred for 2 days until the reaction was complete by TLC. The reaction suspension was neutralized by the addition of 1M HCl and concentrated to a white solid. The white solid was filtered and washed with H2O and ether to yield 0.142 g (44%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): 8.19 (dd, 1H, J=5.2 and 0.8 Hz), 7.79 (s, 1H), 7.52 (dd, 2H, J=8.2 and 6.3 Hz), 7.41 (dd, 1H, J=5.5 Hz), 3.77 (s, 2H), 2.97 (s, 3H).

후처리

  1. concentrationconcentrated to a white solid
  2. filtrationThe white solid was filtered
  3. washwashed with H2O and ether

출처 및 근거

ORD 기록
ord-af59ecf45899413a9c29b922e471c0f3
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144876B2

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