N-Boc-glycine methyl ester → Methyl 2-Boc-8-bromo-4-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 920239

反応式

HRID 920239 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].[Br:20][C:21]1[C:22]([CH2:31]Br)=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24](OC)=[O:25]>CN(C=O)C.C([O-])(O)=O.[Na+].CCOC(C)=O>[Br:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:23]2[C:22]=1[CH2:31][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:24]2=[O:25]

参加物

7

反応物 3

HCID 637609N-Boc-glycine methyl esterHCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 89524864Methyl 2-Boc-8-bromo-4-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a flask containing methyl 2-((tert-butoxycarbonyl)amino)acetate (4.18 g, 22.09 mmol) in anhydrous DMF (50 ml) was added KOtBu (3.99 g, 35.6 mmol) then after 1 min at room temperature added methyl 3-bromo-2-(bromomethyl)benzoate (4.97 g, 16.14 mmol) as a solid in 1 portion. The reaction mixture was then capped (not under N2) & stirred at room temperature for 3 hours. Followed by LC/MS. The reaction mixture was quenched/diluted with sat'd NaHCO3, then suspended in EtOAc, washed with saturated NaHCO3, then H2O, then brine; organics dried over Na2SO4, filtered & concentrated. Purification by silica gel chromatography (0-20% EtOAc/Hex; 220 g ISCO); desired fractions concentrated to yield 2-tert-butyl 3-methyl 8-bromo-4-oxo-3,4-dihydroisoquinoline-2,3 (1H)-dicarboxylate (24-1).

後処理

  1. customThe reaction mixture was then capped (not under N2) &
  2. washwashed with saturated NaHCO3
  3. dry with materialorganics dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (0-20% EtOAc/Hex; 220 g ISCO)
  7. concentrationdesired fractions concentrated

出典と根拠

ORDレコード
ord-876f14f7b15740739fc7604db15edfdf
出典データセット
uspto-grants-2016_03
特許番号
US09273040B2

関連ノート

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