Hydrochloric Acid → 2-(3,4-Bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)acetic acid

HRID 576656

反応式

HRID 576656 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[C:25]([O-:28])([O-])=[O:26].[K+].[K+].[OH-].[Na+].Cl>CN(C=O)C.CO.C1COCC1.O>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:15][CH2:16][NH:17][C:25]([O:28][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[O:24])([CH3:23])([CH3:22])[CH3:21]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 11008556Methyl 3,4-Dihydroxyphenylacetate

生成物 1

HCID 867252812-(3,4-Bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)acetic acid

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To methyl 2-(3,4-dihydroxyphenyl)acetate (1.0 g) in DMF (10 mL) was added tert-butyl 2-bromoethylcarbamate (2.7 g) and K2CO3 (1.7 g). The resulting reaction mixture was stirred at 60° C. overnight. Water was added and the aqueous phase extracted with EtOAc. The organic phase was then dried and concentrated. The residue was purified by flash chromatography. The product was obtained as a mixture of mono- and bis-alkylation. The mixture was then dissolved in MeOH and THF (10 mL, 1:1) and 1N NaOH was added. The resulting reaction mixture was stirred at room temperature overnight. 1N HCl was added to acidify the solution. The aqueous phase was extracted with EtOAc (3×). The organic phases were combined, dried and concentrated. The title product was obtained by reverse phase chromatography purification (0.5 g).

後処理

  1. customThe resulting reaction mixture
  2. extractionthe aqueous phase extracted with EtOAc
  3. customThe organic phase was then dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. customThe product was obtained as a mixture of mono- and bis-alkylation
  7. customThe resulting reaction mixture
  8. stirringwas stirred at room temperature overnight
  9. extractionThe aqueous phase was extracted with EtOAc (3×)
  10. customdried
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-450799883080461790acfd947cb88923
出典データセット
uspto-grants-2015_05
特許番号
US09040504B2

関連ノート

読み込み中…