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

HRID 856983ノート

反応式

HRID 856983 の反応式
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]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2 回HCID 16222813((2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid ethyl ester

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-af59ecf45899413a9c29b922e471c0f3
出典データセット
uspto-grants-2006_12
特許番号
US07144876B2

反応ノート

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