Benzyl Bromide → Boc-Ser-OBzl

HRID 495968

反応式

HRID 495968 の反応式
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:13][C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 98766N-[tert-butoxycarbonyl]-L-serine

生成物 1

HCID 7018792Boc-Ser-OBzl

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a round-bottomed flask were placed N-BocSerine (20.0 g, 89.605 mmol, 1 eq.), benzyl bromide (10.76 ml, 90.50 mmol, 1.01 eq.) and cesium carbonate (56.64 g, 173.84 mmol, 1.94 eq.) in DMF (180 mL). The suspension was stirred under nitrogen at room temperature for 2 hrs to overnight. The mixture was partitioned between water and ethyl acetate (1:1, 1000 ml) and aqueous layer was re-extracted with ethyl acetate(2×200 mL). The combined organic layers were washed with water (2×500 mL), saturated sodium chloride, and dried over sodium sulfate. The solvents were removed in vacuo and the crude material purified on silica gel to get N-Boc-serine benzyl ester.

後処理

  1. customIn a round-bottomed flask were placed
  2. customThe mixture was partitioned between water and ethyl acetate (1:1, 1000 ml) and aqueous layer
  3. extractionwas re-extracted with ethyl acetate(2×200 mL)
  4. washThe combined organic layers were washed with water (2×500 mL), saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customthe crude material purified on silica gel

出典と根拠

ORDレコード
ord-8f0f1a3cf25a48c49844fa18108794ec
出典データセット
uspto-grants-2005_09
特許番号
US06943157B2

関連ノート

読み込み中…