Hydrochloric Acid → (2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

HRID 1887752노트

반응식

HRID 1887752 반응식
[CH3:1][C:2]([NH:38]C(=O)OC(C)(C)C)([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7](=[O:32])[NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:4].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:38][C:2]([CH3:1])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:32])=[O:4]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 44193590tert-butyl 2-methyl-1-[(2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylamino]-1-oxopropan-2-ylcarbamate

생성물 1

HCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

tert-Butyl 2-methyl-1-[(2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylamino]-1-oxopropan-2-ylcarbamate (2.8 g) was dissolved in ethanol (28 mL), and concentrated hydrochloric acid (7.5 mL) was added thereto. The mixture was heated at 70° C. while being stirred for 30 minutes, and then neutralized with saturated aqueous sodium bicarbonate solution under cooling on ice. Subsequently, the resultant mixture was extracted with chloroform and water, and the aqueous layer was further extracted with chloroform. The organic layers were combined. The combined organic layer was washed with saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (2.30 g) was yielded.

후처리

  1. temperatureunder cooling on ice
  2. extractionSubsequently, the resultant mixture was extracted with chloroform and water
  3. extractionthe aqueous layer was further extracted with chloroform
  4. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, whereby the title compound (2.30 g)
  7. customwas yielded

출처 및 근거

ORD 기록
ord-84013b6b36a148e3abe362994e14b75a
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501772B2

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