Sodium Chloride → (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 235732Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH2:17][OH:18])[NH:14][C:13]1=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:22](OC)([CH3:24])[CH3:23].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C:13](=[O:19])[N:14]2[C@@H:15]1[CH2:16][CH2:17][O:18][C:22]2([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one (735 mg) in methylene chloride (30 ml) were added 2,2-dimethoxypropane (0.513 ml) and boron trifluoride etherate (0.026 ml) at 0° C. The mixture was stirred for 10 minutes at 0° C. and for 5 hours at ambient temperature. The reaction mixture was poured into a mixture of methylene chloride (30 ml) and aqueous sodium bicarbonate and sodium chloride (1:1). The organic layer was separated and the aqueous layer was extracted with methylene chloride (20 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (16 g) eluting with a mixture of methylene chloride and acetone (10:1-5:1) to give (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (753 mg) as an oil.

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted with methylene chloride (20 ml)
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel (16 g)
washeluting with a mixture of methylene chloride and acetone (10:1-5:1)

Sources & evidence

ORD record: ord-e1c141a90c3c4e2b86b1b3bf97e2c08c
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640915

Reaction notes

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