2-Methylphenyl isothiocyanate → (4-Methyl-2-o-tolylamino-benzoxazol-6-yl)-acetic acid

HRID 49706노트

반응식

HRID 49706 반응식
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[CH:4][C:3]=1[OH:17].[C:18]1([CH3:27])[C:19]([N:24]=[C:25]=S)=[CH:20][CH:21]=[CH:22][CH:23]=1>C(O)C>[CH3:8][C:7]1[C:2]2[N:1]=[C:25]([NH:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:27])[O:17][C:3]=2[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=1

참가 물질

4

반응물 2

HCID 691952-Methylphenyl isothiocyanateHCID 18188095t-Butyl 4-amino-3-hydroxy-5-methyl-phenylacetate

생성물 1

HCID 18188094(4-Methyl-2-o-tolylamino-benzoxazol-6-yl)-acetic acid수율 69.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of t-butyl 4-amino-3-hydroxy-5-methyl-phenylacetate (0.38 g, Reference Example 10) in ethanol (10 mL) and o-tolylisothiocyanate (0.24 g) was stirred for 7 hours, then left to stand over night and then evaporated. The residue was dissolved in ethanol (10 mL) and the solution was treated with dicyclohexylcarbodiimide (0.36 g). This mixture was heated at reflux temperature for 2 hours and then evaporated. The residual gum was dissolved in dichloromethane (15 mL) and the solution was treated with trifluoroacetic acid (4.75 mL). After standing at room temperature for 3 hours the mixture was evaporated and the residue was dissolved in diethyl ether. This solution was extracted twice with saturated sodium bicarbonate solution and the pH of the combined aqueous extracts was adjusted to 1-2 by addition of dilute hydrochloric acid. This solution was then extracted with ethyl acetate and the extract was washed with brine, then dried and then evaporated to give the title compound (0.33 g) as a pale yellow solid.

후처리

  1. waitleft
  2. waitto stand over night
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethanol (10 mL)
  5. additionthe solution was treated with dicyclohexylcarbodiimide (0.36 g)
  6. temperatureThis mixture was heated
  7. temperatureat reflux temperature for 2 hours
  8. customevaporated
  9. dissolutionThe residual gum was dissolved in dichloromethane (15 mL)
  10. additionthe solution was treated with trifluoroacetic acid (4.75 mL)
  11. waitAfter standing at room temperature for 3 hours
  12. customthe mixture was evaporated
  13. dissolutionthe residue was dissolved in diethyl ether
  14. extractionThis solution was extracted twice with saturated sodium bicarbonate solution
  15. additionthe pH of the combined aqueous extracts was adjusted to 1-2 by addition of dilute hydrochloric acid
  16. extractionThis solution was then extracted with ethyl acetate
  17. washthe extract was washed with brine
  18. customdried
  19. customevaporated

출처 및 근거

ORD 기록
ord-c38f0cc24a4e4187a72395a6890f0e0d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706738B2

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