Sodium Iodide → 2-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester

HRID 1242857ノート

反応式

HRID 1242857 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:15][C:16](=[O:32])[CH2:17][N:18]=[C:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:14])([CH3:13])[CH3:12].Br[CH2:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[F:43].[I-].[Na+]>C1COCC1.CCOCC.CCCCC>[C:11]([O:15][C:16](=[O:32])[CH:17]([N:18]=[C:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[F:43])([CH3:14])([CH3:12])[CH3:13]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2733832Lithium HexamethyldisilazideHCID 218916842-(Bromomethyl)-1-fluoro-4-methoxybenzene

生成物 1

HCID 879214182-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester収率 97%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21877078Diethylether pentane溶媒

実験手順

LHMDS (92 mg, 0.55 mmol) was added to a solution of t-butylglycinate Schiff base 3 (136 mg, 0.46 mmol) in THF (1.5 mL) A mixture containing 2-fluoro-5-methoxy-benzyl bromide (35, 100 mg, 0.46 mmol) and sodium iodide (138 mg, 0.92 mmol) in THF (2.0 mL) was immediately added to the resulting enolate solution at −78° C. The combined mixture was warmed to room temperature, stirred for 2 h, diluted with 1:1 ether/pentane (25 mL), washed with brine (3×15 mL), dried (sodium sulfate) and concentrated to afford 40 as a crude yellow oil (108%). Once examined, the pure product was made in 97% yield (193 mg).

後処理

  1. washwashed with brine (3×15 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-eb0358ba22ef4fc0b8e5754f8286ec8a
出典データセット
uspto-grants-2006_10
特許番号
US07115766B2

反応ノート

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