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

HRID 1180378노트

반응식

HRID 1180378 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da1fcdbca44645f18fa98c05880649b8
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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