Acetic Acid → Azetidon

HRID 2072761Notes

Reaction equation

HRID 2072761 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([O:15][Si](C)(C)C)[NH:13][C:12]1=[O:20])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:21](O)(=[O:23])[CH3:22].C(OC(=O)C)(=O)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:21]([O:15][C@H:14]1[NH:13][C:12](=[O:20])[C@@H:11]1[C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:10])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 13654682HCID 13654682, compound

Product 1

HCID 10935078AzetidonYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

After 155 mg of (3R,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-trimethylsilyloxyazetidin-2-one was dissolved in 1.6 ml of tetrahydrofuran, the mixture was cooled to -35° C. And thereto 0.03 ml (concentration: 1.84% by volume) of acetic acid, 0.5 ml of acetic anhydride and then 20 mg (concentration: 0.92% by weight) of 4-dimethylaminopyridine were added. The mixture was stirred for 22 hours at -35° C. After the same treatment as in Example 16, it was analyzed by means of high performance liquid chromatography used in Example 16 to find 84 mg of (3R,4R)-4-acetoxy-3-[(R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one (yield: 60%).

Sources & evidence

ORD record
ord-a31e8a85819642fbbb6365f4c0fd6480
Source dataset
uspto-grants-1990_04
Patent number
US04914200

Reaction notes

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