4-Nitrophenol → Z-Pyr-ONp

HRID 543248ノート

反応式

HRID 543248 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22](O)[CH:21]=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([O:19][C:22]1[CH:21]=[CH:20][C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 9804-NitrophenolHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

生成物 1

HCID 7408213Z-Pyr-ONp

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

10 g (40 mmol) of N-(benzyloxycarbonyl)-(L)-pyroglutamic acid and 5.84 g (40 mmol) of p-nitrophenol are dissolved in 100 ml of THF. A solution of 8.65 g (42 mmol) of N,N-dicyclohexylcarbodiimide in 40 ml of THF is run in at ordinary temperature, the mixture is stirred for 6 hours and filtered, the filtrate is evaporated, the residue is taken up with ethyl acetate, the mixture is filtered, the filtrate is evaporated and the residue is recrystallized from the same solvent. This gives 60% of a pure product of melting point=141°-2° C.; [α]D25 =-48.7° (C=1, THF).

後処理

  1. filtrationfiltered
  2. customthe filtrate is evaporated
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated
  5. customthe residue is recrystallized from the same solvent
  6. custom[α]D25 =-48.7° (C=1, THF)

出典と根拠

ORDレコード
ord-32af35763de847c0919cbdad45f8c8f0
出典データセット
uspto-grants-1987_04
特許番号
US04661512

反応ノート

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