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

HRID 2250471ノート

反応式

HRID 2250471 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 mL, 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-591a1cbee70f49c8b1cec6ff5d3086bb
出典データセット
uspto-grants-2008_01
特許番号
US07317029B2

反応ノート

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