Sodium hydride → Tert-butyl 4-{4-[[1-(methoxycarbonyl)-3-methylbutoxy](phenyl)methyl]benzoyl}piperazine-1-carboxylate

HRID 1180378ノート

反応式

HRID 1180378 の反応式
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH:33]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:34]([O:36][CH3:37])=[O:35]>CN(C=O)C>[CH3:37][O:36][C:34]([CH:33]([O:1][CH:2]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[O:8])=[CH:22][CH:23]=1)[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 12957039Methyl 2-bromo-4-methylpentanoateHCID 69470269Tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate

生成物 1

HCID 69473035Tert-butyl 4-{4-[[1-(methoxycarbonyl)-3-methylbutoxy](phenyl)methyl]benzoyl}piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate from step 3 (1.5 g, 3.8 mmol) in DMF (20 mL) at 0° C. was added sodium hydride (0.16 g, 4.0 mmol) portionwise. The mixture was aged 15 minutes under a nitrogen atmosphere and methyl 2-bromo-4-methylpentanoate (0.65 mL, 4.0 mmol) was added dropwise. The reaction was allowed to warm to room temperature and was aged for 3 hours. The mixture was then partitioned between ethyl acetate and brine and the organic layer was dried and evaporated. The crude product was chromatographed on silica gel using 40% ethyl acetate in hexanes to afford the title compound.

後処理

  1. waitwas aged for 3 hours
  2. customThe mixture was then partitioned between ethyl acetate and brine
  3. customthe organic layer was dried
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel using 40% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-da1fcdbca44645f18fa98c05880649b8
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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