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Hydrochloric Acid → 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid

HRID 1512946
ノート
印刷プレビュー

反応式

HRID 1512946 の反応式
[OH-].[Na+].[CH3:3][CH:4]([O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:21]4)[N:14]=2)=[CH:9][C:8]=1[C:34]([F:37])([F:36])[F:35])[CH3:5].Cl>C1COCC1.C(O)(C)C.O>[CH3:5][CH:4]([O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:21]4)[N:14]=2)=[CH:9][C:8]=1[C:34]([F:36])([F:37])[F:35])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146129ethyl 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoate

生成物 1

HCID 591461083-(5-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid収率 47.7%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3776Isopropanol溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydroxide (36 mg) was added to a solution of ethyl 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoate (D117) (89 mg) in THF (1 mL), isopropanol (1 mL) and water (0.5 mL). The mixture was stirred at room temperature until LCMS showed no starting material. The mixture was neutralized with 2 M HCl till pH ˜6.0. The crude product was purified by Mass Directed Auto Prep to afford of 3-(5-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-2-yl)propanoic acid (E92) (40 mg). δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.70 (2H, t), 2.99 (2H, t), 5.55 (1H, m), 6.35 (1H, s), 7.46 (1H, d), 7.77 (1H, dd), 8.23 (1H, s), 8.64 (1H, d), 9.22 (1H, d), 11.36 (1H, s), 12.25 (1H, s); MS (ES): C22H19F3N4O4 requires 460; found 461.2 (M+H+).

後処理

  1. customThe crude product was purified by Mass Directed Auto Prep

出典と根拠

ORDレコード
ord-0d339e637155413db8ff64de32adddf1
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217028B2

反応ノート

読み込み中…

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