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Benzyl chloroformate → ((Benzyloxy)carbonyl)-L-allothreonine

HRID 962656
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HRID 962656 반응식
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15].C([O-])(O)=O.[Na+]>O>[C:9]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[C@H:14]([CH3:16])[OH:15])([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 99289Allothreonine, L-HCID 516892Sodium Bicarbonate

생성물 1

HCID 853483((Benzyloxy)carbonyl)-L-allothreonine수율 63%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Benzylchloroformate (0.35 ml; 2.3 mmol) was added to a mixture of L-allothreonine (0.25 g; 2.1 mmol) and NaHCO3 (435 mg; 5.18 mmol) in 2.5 ml of H2O at RT. After 3 h, the reaction mixture was partitioned between Et2O and H2O. The aqueous layer was washed with Et2O, acidified to pH <2 with 6N HCl, and extracted with CH2 Cl2. The organic layer was dried (MgSO4) and concentrated to afford 320 mg (63%) of Cbz-L-allothreonine.

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후처리

  1. customthe reaction mixture was partitioned between Et2O and H2O
  2. washThe aqueous layer was washed with Et2O
  3. extractionextracted with CH2 Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ff152904544448a8a1006271d84d3929
출처 데이터셋
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05760036

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