Methanol → Ethyl 2-(4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolyl)acetate

HRID 256775ノート

反応式

HRID 256775 の反応式
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:16])[C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.BrBr.[CH3:25][NH:26][C:27]([NH2:29])=[S:28].CO.[CH2:32](OCC)[CH3:33]>>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:9]2[N:29]=[C:27]([NH:26][CH3:25])[S:28][C:10]=2[CH2:11][C:12]([O:14][CH2:32][CH3:33])=[O:13])[CH3:16])[CH:5]=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 24408BromineHCID 2723704MethylthioureaHCID 197855665-(2-Fluoro-4-biphenylyl)-4-oxohexanoic acid

生成物 1

HCID 19785542Ethyl 2-(4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolyl)acetate収率 35%

実験手順

To an ice-cooled solution of 5-(2-fluoro-4-biphenylyl)-4-oxohexanoic acid (500 mg, 1.52 mmoles) in diethyl ether (10 ml) was added dropwise bromine (243 mg, 1.52 mmoles) and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated under reduced pressure. A mixture of the afforded residue, N-methylthiourea (164 mg, 1.82 mmoles) and methanol was stirred at 50° C. for 2 hours and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduce pressure. Purification of the residue by medium pressure silica gel column chromatography gave the desired ethyl 2-(4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolyl)acetate (209 mg, 0.524 mmole, yield 35%) as a yellow oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringwas stirred at 50° C. for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the residue by medium pressure silica gel column chromatography

出典と根拠

ORDレコード
ord-4d4587232178424baa5731f6b33f3622
出典データセット
uspto-grants-1993_11
特許番号
US05258396

反応ノート

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