Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate → Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate

HRID 524412노트

반응식

HRID 524412 반응식
C(OC([N:8](CC1C=CC(OC)=CC=1)[C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:20][CH:21]([CH3:22])[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1

참가 물질

3

반응물 1

HCID 68182441Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate

생성물 1

HCID 86669546Ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate수율 75%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate (0.55 g, 1.2 mmol) was dissolved in TFA (7 mL). The reaction mixture was refluxed for 5 hours. TFA was removed under reduced pressure. The residue was diluted with water (10 mL) and ethyl acetate (15 mL) and basified with sodium bicarbonate. The organic layer was separated and aqueous layer was again extracted with ethyl acetate (15 mL). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to obtain crude product which was purified by silica gel column chromatography using 20% ethyl acetate in hexane to provide ethyl 2-(2-aminothiazol-4-yl)-2-isopropoxy-acetate (0.22 g).

후처리

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customTFA was removed under reduced pressure
  3. additionThe residue was diluted with water (10 mL) and ethyl acetate (15 mL)
  4. customThe organic layer was separated
  5. extractionaqueous layer was again extracted with ethyl acetate (15 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude product which
  10. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b13024cc75f94df3a5a9b41b2a08af00
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340506B2

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