Carbon Dioxide → ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate

HRID 1779195

反応式

HRID 1779195 の反応式
[CH2:1]([O:3][C:4](=[O:22])[C@H:5]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]#[C:32][CH3:33].[Cl-].[NH4+].C(=O)=O>CN(C=O)C>[C:10]([O:9][C:7]([NH:6][C@@H:5]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:30][C:31]#[C:32][CH3:33])=[CH:17][CH:16]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:22])=[O:8])([CH3:13])([CH3:11])[CH3:12]

参加物

7

反応物 5

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 27568621-Bromo-2-butyneHCID 11077750Ethyl N-(tert-butoxycarbonyl)-L-tyrosinate

生成物 1

HCID 90060290ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate収率 96.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In dehydrated DMF (5.0 mL) was dissolved 1.35 g (4.23 mmol) of Boc-L-tyrosine ethyl ester (AK Scientific, Inc catalogue No 71054), and anhydrous potassium carbonate (0.7 g, 5.08 mmol) and 1-bromo-2-butyne (0.619 g, 4.65 mmol) were added at room temperature. The mixture was stirred under argon atmosphere for 21 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added to the reaction solution until generation of carbon dioxide gas stopped. This reaction solution was extracted with ethyl acetate, and washed with water and a saturated brine in this order. The extracted organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The obtained oily residue was purified by silica gel chromatography (20 g cartridge was used) using 10% ethyl acetate/n-hexane as an elution solvent to obtain 1.47 g (92% yield) of the title compound as clear and colorless oil.

後処理

  1. additionwere added at room temperature
  2. extractionThis reaction solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe extracted organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customThe obtained oily residue was purified by silica gel chromatography (20 g cartridge was used)

出典と根拠

ORDレコード
ord-3dc25f3e4aaa4892bad5e2e12fd4aaa2
出典データセット
uspto-grants-2016_02
特許番号
US09266853B2

関連ノート

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