Acetic Acid → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one

HRID 1075647Notes

Reaction equation

HRID 1075647 reaction equation
CC(O)=O.[C:5]1([CH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]2[C@@H:30]([O:31][CH:32]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:33][O:34][Si](C(C)(C)C)(C)C)[NH:29][C:28]2=[O:48])=[O:25])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CO.C(OCC)(=O)C>C1COCC1>[C:5]1([CH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]2[C@@H:30]([O:31][CH:32]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:33][OH:34])[NH:29][C:28]2=[O:48])=[O:25])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21584119Ethylacetate methanolHCID 70094998(3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyidimethylsilyl)oxy-1-phenyl ethoxy}-azetidin-2-one

Product 1

HCID 70096759(3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-oneYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of 1 N BU4NF (0.84 ml, 0.84 mmole) containing AcOH (35 mg, 0.56 mmole) was added to a solution of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyldimethylsilyl)oxy-1-phenylethoxy}-azetidin-2-one (430 mg, 0.70 mmole) in THF (5 ml) at 0-5° C. The mixture was stirred at room temperature for 3 hrs, then poured into a silica gel column. The column was eluented with methanol-ethyl acetate (5:95) and 260 mg of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one was obtained (74% yield).

Workup

  1. additionpoured into a silica gel column

Sources & evidence

ORD record
ord-3e858de6056f41f19c9b570911c808be
Source dataset
uspto-grants-1999_05
Patent number
US05905076

Reaction notes

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