Bromopinacolone → (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

HRID 1908626ノート

反応式

HRID 1908626 の反応式
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([OH:22])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[H-].[Na+].Br[CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[N:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

参加物

6

反応物 3

HCID 21642BromopinacoloneHCID 24758Sodium hydrideHCID 178501468HCID 178501468、化合物

生成物 1

HCID 66920060(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 6.5 g of (S)-2-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester in 175 ml of DMF was cooled to 0° C. Then, 644 mg of sodium hydride (60% in mineral oil) was added portionwise over 20 min. Further 20 min after completion of the addition 2.9 g of 1-Bromo-3,3-dimethyl-butan-2-one was added and the reaction mixture was allowed to warm to RT. After striring for 16 h the reaction mixture was diluted with brine and extracted with DCM. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 3.3 g.

後処理

  1. additionwas added
  2. extractionextracted with DCM
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  6. additionThe fractions containing the product
  7. customthe solvent evaporated under reduced pressure

出典と根拠

ORDレコード
ord-2b6f2a15ef2642cf8114976875df67f5
出典データセット
uspto-grants-2013_12
特許番号
US08598179B2

反応ノート

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