Triethylamine → HCID 89824779, 화합물

HRID 2277086노트

반응식

HRID 2277086 반응식
[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6](Cl)=[O:7])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:20]([O:24][C:25](=[O:45])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH2:35][NH:36][C:37]([C@@H:39]1[CH2:44][CH2:43][CH2:42][CH2:41][NH:40]1)=[O:38])([CH3:23])([CH3:22])[CH3:21]>C1COCC1>[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([N:40]1[CH2:41][CH2:42][CH2:43][CH2:44][C@H:39]1[C:37](=[O:38])[NH:36][CH2:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:25]([O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:45])=[O:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 89824898HCID 89824898, 화합물HCID 89835603HCID 89835603, 화합물

생성물 1

HCID 89824779HCID 89824779, 화합물수율 64.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cooled (−10° C.) solution of (2R)-1-chloro-3,3-dimethyl-1-oxobutan-2-yl acetate (0.15 g, 0.82 mmol) in THF (5 mL) was added triethylamine (0.54 mL, 3.90 mmol) and a solution of (S)-tert-Butyl-4-chloro-2-{(piperidine-2-carboxamido)methyl}benzylcarbamate (0.3 g, 0.78 mmol) in THF (2 mL) at −10° C. The reaction mixture was stirred at room temperature for 1 h then quenched with water (50 mL) and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by reverse phase combiflash column chromatography (C18, eluent: 0-10% acetonitrile water) to afford the title compound (0.27 g) as a white solid.

후처리

  1. customat −10° C
  2. customthen quenched with water (50 mL)
  3. extractionextracted with EtOAc (3×25 mL)
  4. washThe combined organic extracts were washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase combiflash column chromatography (C18, eluent: 0-10% acetonitrile water)

출처 및 근거

ORD 기록
ord-d98c0eb35f454531b62703ba0f371951
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133147B2

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