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

HRID 848522

反応式

HRID 848522 の反応式
[C:1]([NH:11][CH: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].S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:23]=1[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[O:25]>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH:12]([C:14](=[O:16])[NH:21][C:22]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:23]=1[C:24](=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[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 24386Thionyl ChlorideHCID 676572-Amino-2'-fluoro-5-nitrobenzophenoneHCID 95657N-(Benzyloxycarbonyl)-DL-alanine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

50 g of carbobenzoxy-DL-alanine are dissolved in 400 ml of absolute tetrahydrofuran, treated dropwise while cooling with ice with 30 g of thionyl chloride and stirred for 40 minutes, a suspension of 50 g of 2-amino-5-nitro-2'-fluorobenzophenone in 200 ml of absolute tetrahydrofuran then being rapidly added dropwise. Subsequently, the mixture is stirred at room temperature for 18 hours, the solution is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution. The mixture is extracted with methylene chloride, the organic solution is dried with sodium sulphate, filtered and concentrated. The residue is crystallised from ethanol and yields rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate which is further processed directly as the crude product.

後処理

  1. additiontreated dropwise
  2. additionthen being rapidly added dropwise
  3. stirringSubsequently, the mixture is stirred at room temperature for 18 hours
  4. concentrationthe solution is concentrated
  5. additionthe residue is treated with ice and 10% sodium bicarbonate solution
  6. extractionThe mixture is extracted with methylene chloride
  7. dry with materialthe organic solution is dried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is crystallised from ethanol

出典と根拠

ORDレコード
ord-d7a69e9e3dc244e2a5f268bf7949bb71
出典データセット
uspto-grants-1981_10
特許番号
US04296031

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