Thionyl Chloride → Benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate

HRID 1155122ノート

反応式

HRID 1155122 の反応式
[C:1]([NH:11][CH:12]([C:17]([OH:19])=O)[CH2:13][CH2:14][CH2:15]C)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])=[O:28]>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH:12]([C:17](=[O:19])[NH:24][C:25]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:26]=1[C:27](=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])[CH2:13][CH2:14][CH3:15])[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 263476N-[(Benzyloxy)carbonyl]norleucine

生成物 1

HCID 131712305Benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

19.7 g of N-carbobenzoxy-DL-norleucine are dissolved in 200 ml of absolute tetrahydrofuran, the solution is treated dropwise while cooling with ice with 10 g of thionyl chloride and then stirred for 1 hour. To this solution there is rapidly added dropwise a solution of 17 g (0.065 M) of 2-amino-5-nitro-2'-fluorobenzophenone in 130 ml of absolute tetrahydrofuran and the mixture is then stirred at room temperature for 60 hours. The solution is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried with sodium sulphate, filtered and concentrated. The residue is purified on a 450 g silica gel column using methylene chloride as the eluting agent and crystallised from ethanol. There is obtained benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate which melts at 148°-150° C.

後処理

  1. additionthe solution is treated dropwise
  2. stirringthe mixture is then stirred at room temperature for 60 hours
  3. concentrationThe solution is concentrated
  4. additionthe residue is treated with ice and 10% sodium bicarbonate solution
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic solution is dried with sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified on a 450 g silica gel column
  10. customcrystallised from ethanol

出典と根拠

ORDレコード
ord-a135f2e9d13f4b2b955cf2cb3b981ecb
出典データセット
uspto-grants-1981_11
特許番号
US04299767

反応ノート

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