Phosphorus pentachloride → Rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate

HRID 437336

反応式

HRID 437336 の反応式
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:23][C:24]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:25]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34])=[O:27]>C(Cl)Cl>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH:12]([C:14](=[O:16])[NH:23][C:24]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:25]=1[C:26](=[O:27])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34])[CH3:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 24819Phosphorus pentachlorideHCID 676572-Amino-2'-fluoro-5-nitrobenzophenoneHCID 736104N-carbobenzyloxyalanine

生成物 1

HCID 20562333Rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-40 °C

実験手順

90 g of carbobenzoxy-L-alanine are dissolved in 500 ml of absolute methylene chloride, the solution is cooled to -40° C and treated with 95 g of phosphorus pentachloride. The mixture is stirred at -30° C for 20 minutes and subsequently added to a shaken solution of 52 g of 2-amino-5-nitro-2'-fluorobenzophenone in 250 ml of absolute methylene chloride. The solution is concentrated on a rotary evaporator at 50°-60° C, treated twice with toluene and evaporated each time. By crystallisation of the residue from ether, there is obtained (-)-benzyl-[1-[{2-(o-fluorobenzoyl)-4-nitrophenyl}-carbamoyl]ethyl]carbamate which melts at 158°-160° C and exhibits a rotation of [α]25D =-23.4° (in methylene chloride, 1%).

後処理

  1. concentrationThe solution is concentrated on a rotary evaporator at 50°-60° C
  2. additiontreated twice with toluene
  3. customevaporated each time
  4. customBy crystallisation of the residue from ether

出典と根拠

ORDレコード
ord-d4a04a459fb242ab8e26b0f21751110e
出典データセット
uspto-grants-1977_06
特許番号
US04031078

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