Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate → 2-(4-(4-(3-(2-Chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

HRID 1024450ノート

反応式

HRID 1024450 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:22]([NH:24][CH:25]([CH:30]([CH3:32])[CH3:31])[C:26]([O:28]C)=[O:27])=[O:23])[S:20][CH:21]=2)=[CH:13][CH:12]=1>C1COCC1.O.[OH-].[Li+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:33])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:22]([NH:24][CH:25]([CH:30]([CH3:31])[CH3:32])[C:26]([OH:28])=[O:27])=[O:23])[S:20][CH:21]=2)=[CH:13][CH:12]=1

参加物

4

反応物 1

HCID 52934823Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

生成物 1

HCID 529348242-(4-(4-(3-(2-Chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 168937Lithium hydroxide, monohydrate溶媒

実験手順

To methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 23, 120 mg) in THF (2 ml), 1N lithium hydroxide monohydrate (1.2 ml) was added and reaction mixture was stirred for 16 hours at RT. Organic solvent was concentrated and added water, dilute HCl was added under stirring to pH acidic. The reaction mixture was filtered, and the residue was washed by water, and dried. The residue was dissolved in acetone, pet ether was added, solid was filtered and dried obtain title compound as solid. Yield: 70 mg (60%). 1H NMR (DMSO-d6, 300 MHz): δ 12.98 (bs, 1H), 9.59 (s, 1H), 8.48 (d, 1H), 8.35 (s, 1H), 8.30 (s, 1H), 8.17 (d, 1H), 8.03 (d, 2H), 7.58 (d, 2H), 7.46 (d, 1H), 7.30 (t, 1H), 7.02 (t, 1H), 4.33 (s, 1H), 2.26 (s, 1H), 0.98 (d, 6H).

後処理

  1. customreaction mixture
  2. concentrationOrganic solvent was concentrated
  3. additionadded water, dilute HCl
  4. additionwas added
  5. stirringunder stirring
  6. filtrationThe reaction mixture was filtered
  7. washthe residue was washed by water
  8. customdried
  9. dissolutionThe residue was dissolved in acetone
  10. additionpet ether was added
  11. filtrationsolid was filtered
  12. customdried

出典と根拠

ORDレコード
ord-d226652f6d66410e9adf069bd05ca6d9
出典データセット
uspto-grants-2014_05
特許番号
US08722901B2

反応ノート

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