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Hydrochloric Acid → 3-Methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoic acid

HRID 1024436
ノート
印刷プレビュー

反応式

HRID 1024436 の反応式
[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)=[O:24])=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].Cl>C1COCC1>[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=3)=[O:24])=[CH:20][CH:21]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([OH:6])=[O:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 52933905Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoate

生成物 1

HCID 529339043-Methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

To a solution of methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl) oxazole-2-carboxamido)butanoate (Example 1, 150 mg) in THF (3 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.6 ml) and the mixture was stirred for 4 hours at RT. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4, concentrated under reduced pressure and then crystallized in EtOAc to give the title compound. Yield: 125 mg (85%); 1H NMR (DMSO-d6, 300 MHz): δ 12.93 (bs, 1H), 9.14 (s, 1H), 9.06 (s, 1H), 8.64 (d, 1H), 8.03 (d, 1H), 7.81 (s, 1H), 7.8 (d, 2H), 7.64 (d, 2H), 7.58 (dd, 1H), 7.52 (dd, 1H), 7.34 (m, 1H), 4.28, (m, 1H), 2.26 (m, 1H), 0.95 (d, 6H); MS (ES+) m/z 491 (M+1).

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customcrystallized in EtOAc

出典と根拠

ORDレコード
ord-436d933d57a249bcaa38a223e34be616
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722901B2

反応ノート

読み込み中…

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