Triethylamine → HCID 13599173, 화합물

HRID 127626노트

반응식

HRID 127626 반응식
[C:1]([O:5][C:6](=[O:14])[CH2:7][NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22]([S:25][CH2:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])(=[O:24])[CH3:23]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]([C:28](=[O:29])[CH:27]([CH3:31])[CH2:26][S:25][C:22](=[O:24])[CH3:23])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 13298943Tert-butyl 2-(cyclopentylamino)acetate

생성물 1

HCID 13599173HCID 13599173, 화합물수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred and chilled (0°-5° C.) solution of N-cyclopentylglycine t-butyl ester (60 g, 0.3 mol) and triethylamine (75 ml, 0.5 mol) in methylene chloride (200 ml) was added dropwise 3-acetylthio-2-methylpropanoyl chloride (54 g, 0.3 mol) dissolved in methylene chloride (250 ml). The reaction mixture was stirred overnight. It was filtered free of solid material which was then washed with fresh methylene chloride. Washings and filtrate were combined and concentrated. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate (1000 ml), brine (600 ml), 5% HCl (3×500 ml), brine (500 ml), saturated sodium bicarbonate (5×500 ml). The organic layer was now separated, dried (Na2SO4 and MgSO4), filtered and concentrated to yield the desired product (80.1 g, 78%) as a brown oil.

후처리

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationIt was filtered free of solid material which
  3. washwas then washed with fresh methylene chloride
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate (1000 ml), brine (600 ml), 5% HCl (3×500 ml), brine (500 ml), saturated sodium bicarbonate (5×500 ml)
  7. customThe organic layer was now separated
  8. dry with materialdried (Na2SO4 and MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a051afa5795a42cd85a9cfd34eda75a3
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256761

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