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

HRID 1478885

反応式

HRID 1478885 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+].O>CN(C=O)C.CO.[OH-].[Na+].Cl.C1COCC1>[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 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 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 5

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide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 IN NaOH was added. The resulting reaction mixture was stirred at room temperature overnight. IN 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-c12e81b672324999a5c61d59ee958931
出典データセット
uspto-grants-2016_08
特許番号
US09403850B2

関連ノート

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