Triethylamine → HCID 67437196、化合物

HRID 1968882ノート

反応式

HRID 1968882 の反応式
[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]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 67114406HCID 67114406、化合物HCID 67436431HCID 67436431、化合物

生成物 1

HCID 67437196HCID 67437196、化合物収率 80%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-6b0204a809594c85ad2af734bdd7646e
出典データセット
uspto-grants-2013_04
特許番号
US08426414B2

反応ノート

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