Triethylamine → HCID 67437196, 화합물

HRID 1968882노트

반응식

HRID 1968882 반응식
[F:1][C:2]1[N:7]=[C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][NH:27][C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][N:27]([C:28]1[CH:29]=[CH:30][C:31]([Br:34])=[CH:32][CH:33]=1)[C:11]([C@@H:9]1[CH2:10][C@H:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)=[O:13])[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:16])([CH3:17])[CH3:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 67114406HCID 67114406, 화합물HCID 67436431HCID 67436431, 화합물

생성물 1

HCID 67437196HCID 67437196, 화합물수율 80%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

실험 절차

A mixture of trans-2-(6-fluoro-pyridin-2-yl)-cyclopropanecarboxylic acid (120 mg, 0.55 mmol) in thionyl chloride (2 mL) was heated at reflux for over night. The mixture was concentrated and dried under high vacuum for 3 h. Then the residue was dissolved in DCM (3 mL) and added dropwise to a solution of {(1S,2S)1-[(4-Bromo-phenylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (205 mg, 0.55 mmol) and triethyl amine (153 uL, 1.1 mmol) in DCM (3 mL). The resulting mixture was stirred at rt for overnight. The reaction mixture was concentrated and the residue was subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.) to give the desired product (235 mg, 80%). MS (MH+ 534 and 536).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for over night
  3. concentrationThe mixture was concentrated
  4. customdried under high vacuum for 3 h
  5. dissolutionThen the residue was dissolved in DCM (3 mL)
  6. concentrationThe reaction mixture was concentrated
  7. customwas subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.)

출처 및 근거

ORD 기록
ord-6b0204a809594c85ad2af734bdd7646e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426414B2

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