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1-Hydroxybenzotriazole → 3-({[N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoseryl]amino}methyl)-5-methyl-1,2-oxazole

HRID 1519681
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HRID 1519681 반응식
[C:1]([O:5][C:6]([N:8]([CH3:18])[C@H:9]([C:15]([OH:17])=O)[C:10](=[O:14])[O:11][CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20]1[O:24][N:23]=[C:22]([CH2:25][NH2:26])[CH:21]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]([CH3:18])[C@H:9]([C:15]([NH:26][CH2:25][C:22]1[CH:21]=[C:20]([CH3:19])[O:24][N:23]=1)=[O:17])[C:10](=[O:14])[O:11][CH2:12][CH3:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 86679248N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoserine2회

생성물 1

HCID 71268225
3-({[N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoseryl]amino}methyl)-5-methyl-1,2-oxazole
수율 67.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoserine (Intermediate 7-1, 2.3 g), 1-(5-methyl-1,2-oxazol-3-yl)methanamine (1.0 g), WSC.HCl (2.4 g), HOBt.H2O (1.9 g), and chloroform (24 mL) were stirred overnight at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the desiccant was filtered out. Then, the solvent was distilled off under reduced pressure, and the resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=98/2→92/8) to obtain 3-({[N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoseryl]amino}methyl)-5-methyl-1,2-oxazole (pale yellow oil) (2.1 g, 67%).

후처리

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=98/2→92/8)

출처 및 근거

ORD 기록
ord-45c83e20d2754f20970fbf900c7a05b2
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073821B2

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