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

HRID 1519681Notes

Reaction equation

HRID 1519681 reaction equation
[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]

Participants

8

Reactant 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-oxoserine2×

Product 1

HCID 712682253-({[N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoseryl]amino}methyl)-5-methyl-1,2-oxazoleYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-45c83e20d2754f20970fbf900c7a05b2
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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