Phosgene → 4-tert-Butyl hydrogen L-aspartate

HRID 874083ノート

反応式

HRID 874083 の反応式
O[NH:2][C@H:3]([C:12](N)=[O:13])[CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(Cl)(Cl)=[O:16]>C1COCC1>[NH2:2][C@H:3]([C:12]([OH:13])=[O:16])[CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

参加物

4

反応物 2

HCID 6371PhosgeneHCID 131732572HO-Asp(But)-NH2

生成物 1

HCID 70105704-tert-Butyl hydrogen L-aspartate収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

HO-Asp(But)-NH2 (20.0 g, 105.7 mmol) was suspended in 300 mL of anhydrous THF and heated to 50° C. Phosgene (20% in toluene) (105 mL, 211.4 mmol) was added to the amino acid suspension, and the amino acid dissolved over the course of approx. 1 hr, forming a clear solution. The solution was concentrated on by rotary evaporation, transferred to a beaker, and hexane was added to precipitate the product. The white solid was isolated by filtration and dissolved in anhydrous THF. The solution was filtered over a bed of Celite to remove any insoluble material. An excess of hexane was added on the top of the filtrate and the bilayer solution was left in the freezer overnight. The NCA was isolated by filtration and dried in vacuo. 15.0 g (66% yield) of Asp(But) NCA was isolated as a white, crystalline solid. 1H NMR (d6-DMSO) δ 8.99 (1H), 4.61 (1H), 2.93 (1H), 2.69 (1H), 1.38 (9H) ppm.

後処理

  1. customforming a clear solution
  2. concentrationThe solution was concentrated on by rotary evaporation
  3. additionwas added
  4. customto precipitate the product
  5. customThe white solid was isolated by filtration
  6. filtrationThe solution was filtered over a bed of Celite
  7. customto remove any insoluble material
  8. additionAn excess of hexane was added on the top of the filtrate
  9. customThe NCA was isolated by filtration
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-02cf756427c64302ae3bc70d9c69dfeb
出典データセット
uspto-grants-2015_03
特許番号
US08980326B2

反応ノート

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