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Water → FMOC-Ser(O-Bzl) oxazolidin-4-one

HRID 1463650
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HRID 1463650 반응식
[NH:1]([C:15]([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC(S(O)(=O)=[O:39])=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH:1]([C:15]([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[O:17]1[CH2:18][C:19](=[O:39])[NH:1][CH2:15]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7017914Fmoc-O-benzyl-L-serine

생성물 1

HCID 131717342FMOC-Ser(O-Bzl) oxazolidin-4-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of FMOC-Ser(O-Bzl) (4.16 g), paraformaldahyde (2.0 g), and p-toluenesulfonic acid (0.2 g) in toluene (400 ml) was heated under reflux with azeotropic water removal for 45 min. The solution was cooled, diluted with ethyl acetate (250 ml) and washed three times with 5% aqueous NaHCO3, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with (8:2) hexane:ethyl acetate to give FMOC-Ser(O-Bzl)-oxazolidin-4-one as a crystalline product, m.p. 108°-109° C. Fab Mass spec. m/e 430(M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureThe solution was cooled
  3. washwashed three times with 5% aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with (8:2) hexane

출처 및 근거

ORD 기록
ord-c0c2817622e9492f97dbbdfe8d98b334
출처 데이터셋
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05300492

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