m-Chloroperbenzoic acid → (3S, 4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-carboxymethyl-azetidin-2-one

HRID 64813Notes

Reaction equation

HRID 64813 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Si:12]([N:19]1[CH:22]([CH2:23][C:24](=[O:29])[Si](C)(C)C)[CH:21]([C@H:30]([OH:32])[CH3:31])[C:20]1=[O:33])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[Si:12]([N:19]1[C@H:22]([CH2:23][C:24]([OH:9])=[O:29])[C@@H:21]([C@H:30]([OH:32])[CH3:31])[C:20]1=[O:33])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131713054HCID 131713054, compound

Product 1

HCID 12882114(3S, 4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-carboxymethyl-azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

m-Chloroperbenzoic acid (1.00 mmol) is added to a solution of (3S,4R)-1-(t-butyldimethylsilyl-3-[(R)-1-hydroxyethyl]-4-(2-oxo-2-trimethylsilylethyl)azetidin-2-one (1.00 mmol) in chloroform (4 ml). The resulting solution is heated at reflux for 4 hr, then cooled, concentrated in vacuo, and the residue chromatographed on silica gel (2% glacial acetic acid in methylene chloride). (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-carboxymethyl-azetidin-2-one, 238 mg (83%) is isolated as a colorless solid, Rf =0.25. n.m.r. (CDCl3 & D2O) δ 3.6-4.3 (2H, m, H-5, H-8), δ 2.98 (1H, dd, J=7, 2.1H-6), δ 2.7 (2H,d of ABq)-CH2CO2H), δ 1.29 (3H, d, J=6, CH3 --) δ 0.95 (9H, S, Si±), δ 0.25 (6H, S, (CH3)2 -Si).

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux for 4 hr
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on silica gel (2% glacial acetic acid in methylene chloride)

Sources & evidence

ORD record
ord-f9ddb18566b141a1bb09a2673921e4f9
Source dataset
uspto-grants-1986_09
Patent number
US04610820

Reaction notes

Loading…