Carbon tetrabromide → N-Boc-beta-bromoalanine benzyl ester

HRID 495969

反応式

HRID 495969 の反応式
[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19]O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19][Br:23])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7018792Boc-Ser-OBzl

生成物 1

HCID 11772725N-Boc-beta-bromoalanine benzyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

The N-Boc-serine benzyl ester was brought up in dichloromethane (170 mL) and treated with carbon tetrabromide (26.37 g, 79.51 mmol, 1.2 eq.), and triphenylphosphine (25.20 g, 96.08 mmol, 1.45 eq.) and the solution was stirred at 0° C. for 30 min. The volatiles were then evaporated in vacuo and the residue was triturated with ether (1000 mL). The solid that separated out was filtered off and organic layer was evaporated in vacuo to get the crude product. The crude material was purified by flash chromatography on silica gel to get N-Boc-β-bromoalanine benzyl ester.

後処理

  1. customThe volatiles were then evaporated in vacuo
  2. customthe residue was triturated with ether (1000 mL)
  3. customThe solid that separated out
  4. filtrationwas filtered off
  5. customorganic layer was evaporated in vacuo
  6. customto get the crude product
  7. customThe crude material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-261e6dacfb0e404994c4a29fb1237969
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…