Potassium Carbonate → 4-[2-(3-Bromo-4-chloro-benzoylamino)-3-methyl-phenoxy]-butyric acid tert-butyl ester

HRID 448863

反応式

HRID 448863 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15])=[O:6].Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:27]([O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[NH:7][C:5](=[O:6])[C:4]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Br:1])[CH:3]=1)([CH3:30])([CH3:29])[CH3:28]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 686028573-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide

生成物 1

HCID 686025154-[2-(3-Bromo-4-chloro-benzoylamino)-3-methyl-phenoxy]-butyric acid tert-butyl ester収率 63.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide (11.3 g, 33.2 mmol), t-butyl 4-bromobutyrate (8.2 g, 36.6 mmol) and K2CO3 (9.2 g, 66.5 mmol) was heated in DMF (100 mL) at 60° C. for 14 hrs. The mixture was then concentrated to remove DMF and partitioned between ethyl acetate and water. The organic layer was separated and washed with water and brine, dried over MgSO4, then purified by silica gel column chromatography eluting with ethyl acetate/hexane (1/4) to yield a red solid, which was further washed with ether to produce a white powder as 4-[2-(3-bromo-4-chloro-benzoylamino)-3-methyl-phenoxy]-butyric acid tert-butyl ester (10.2 g). MS [M-(t-Bu)+H]+: 425.8/427.8; tR=2.79 min. (method 1)

後処理

  1. concentrationThe mixture was then concentrated
  2. customto remove DMF
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. custompurified by silica gel column chromatography
  8. washeluting with ethyl acetate/hexane (1/4)
  9. customto yield a red solid, which
  10. washwas further washed with ether

出典と根拠

ORDレコード
ord-dddc61b4f6684b5387f8128a96133a13
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

関連ノート

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