Benzyl chloroformate → Z-Glu(ome)-OH

HRID 429888

반응식

HRID 429888 반응식
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[O:4].C([O-])(O)=O.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[CH2:21]([O:20][C:18]([NH:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 686625-Methyl hydrogen L-glutamateHCID 516892Sodium Bicarbonate

생성물 1

HCID 6350584Z-Glu(ome)-OH수율 92%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a 1 L 3-necked flask equipped with a thermometer and a magnetic stirrer were added 4.90 g of L-glutamic acid γ-methyl ester (Sigma) and 200 mL of water. The solution was heated to 60° C., treated with 6.40 g of NaHCO3 followed by 5.20 mL of benzyl chloroformate (Aldrich) and allowed to cool to RT with vigorous stirring. After 4 h the reaction mixture was extracted with ethyl ether (4×100 mL) and the ether extracts were discarded. The aqueous solution was acidified to a congo red endpoint by addition of concentrated HCl. An oily emulsion resulted which was extracted with CH2Cl2 (4×60 mL). The combined organic extracts were washed with 0.05 N aqueous HCl (2×60 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to afford 8.23 g (92%) of N-((benzyloxy)carbonyl)-5-O-methyl-L-glutamic acid as a white crystalline solid, m.p. 61-63° C.

후처리

  1. customTo a 1 L 3-necked flask equipped with a thermometer and a magnetic stirrer
  2. temperatureto cool to RT with vigorous stirring
  3. extractionAfter 4 h the reaction mixture was extracted with ethyl ether (4×100 mL)
  4. additionThe aqueous solution was acidified to a congo red endpoint by addition of concentrated HCl
  5. customAn oily emulsion resulted which
  6. extractionwas extracted with CH2Cl2 (4×60 mL)
  7. washThe combined organic extracts were washed with 0.05 N aqueous HCl (2×60 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3b5fc43e8dc94e10b5060f57fe73d0a2
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319702B1

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