Hydrochloric Acid → Z-Leu-phe-OH

HRID 1757136노트

반응식

HRID 1757136 반응식
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([O:20]CC)=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+].Cl>CO>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14562839Z-Leu-Phe-COOEt

생성물 1

HCID 7408339Z-Leu-phe-OH

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
5 °C

실험 절차

Dipeptide Ketoacids (General Procedure). To a stirred solution of 0.53 g (1,13 mmol) Z-Leu-Phe-COOEt in 6.0 ml methanol was added 1.27 ml (1.27 mmol) 1M NaOH. The color of the reaction mixture turned dark yellow and a small amount of solid was deposited. The reaction was run at room temperature and progress of the hydrolysis was checked on TLC. After 24 h. no more substrate was detected. The reaction mixture was chilled in one ice bath at 5° C., acidified with 1M HCl to pH=3 and extracted with AcOEt (2×50 mL). The organic extract were washed with 2×50 ml H2O and if necessary, decolorized with carbon and dried over MgSO4. After evaporation of the solvent (rotavaporator), the residue (thick oil) were titurated with 2×25 ml n-hexane and dried in vacuo. Yield 0.39 g (78%) of colorless, very thick oil. TLC, main spot at Rf =0.24, trace of impurity at Rf =0.78, I. Mass spectrum, FB-MS [(M+1)/Z]=441.

후처리

  1. customwas run at room temperature
  2. extractionextracted with AcOEt (2×50 mL)
  3. extractionThe organic extract
  4. washwere washed with 2×50 ml H2O
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent (rotavaporator)
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-35402ca5deb04b188fadc500cfe020e8
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05444042

반응 노트

불러오는 중…