Hydrochloric Acid → Ethyl 3-chloro-6-(pivalamidomethyl)picolinate

HRID 1469713노트

반응식

HRID 1469713 반응식
C(O[C:6]([NH:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13]([Cl:21])=[CH:12][CH:11]=1)=[O:7])(C)(C)C.Cl.[C:23](Cl)(=O)[C:24](C)([CH3:26])[CH3:25]>CCOC(C)=O>[Cl:21][C:13]1[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:24]([CH3:26])([CH3:25])[CH3:23])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 86692224Ethyl 6-(((tert-butoxycarbonyl)amino)methyl)-3-chloropicolinate

생성물 1

HCID 86692225Ethyl 3-chloro-6-(pivalamidomethyl)picolinate수율 89.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of ethyl 6-(((tert-butoxycarbonyl)amino)methyl)-3-chloropicolinate (100 mg, 0.318 mmol) in EtOAc saturated with HCl (1 mL) was stirred at rt for 1 h. The reaction mixture was concentrated and the concentrate was dissolved in CH2Cl2 (2 mL). The solution was treated with DIPEA (0.5 mL) followed by pivaloyl chloride (38 mg, 0.318 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc and was washed with H2O and brine. The organic layer was separated, dried, filtered and concentrated to afford 85 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (br t, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H), 4.40-4.31 (m, 4H), 1.33-1.10 (m, 12H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in CH2Cl2 (2 mL)
  3. additionThe solution was treated with DIPEA (0.5 mL)
  4. washwas washed with H2O and brine
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0cae618dd96d423381c2b09bec0f53c4
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

반응 노트

불러오는 중…