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 1024450노트

반응식

HRID 1024450 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 168937Lithium hydroxide, monohydrate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d226652f6d66410e9adf069bd05ca6d9
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722901B2

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