4-Nitrophenol → Z-Pyr-ONp

HRID 543248노트

반응식

HRID 543248 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 7408213Z-Pyr-ONp

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-32af35763de847c0919cbdad45f8c8f0
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04661512

반응 노트

불러오는 중…