Sodium Chloride → HCID 13366882, compound

HRID 1632941Notes

Reaction equation

[CH3:1][C:2]([CH3:14])([O:4][C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[NH:10][C:9]1=[O:13])=[O:6])[CH3:3].C([Li])CCC.[CH2:20]([O:22][P:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26])[CH3:21].[Cl-].[Na+]>O1CCCC1>[CH3:12][C@@H:11]1[N:10]([P:23](=[O:27])([O:24][CH2:25][CH3:26])[O:22][CH2:20][CH3:21])[C:9](=[O:13])[C@H:8]1[NH:7][C:5]([O:4][C:2]([CH3:1])([CH3:14])[CH3:3])=[O:6]

Participants

Conditions

Temperature: -78 °C

Procedure

(3S-trans)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-azetidinone (4.6 g) was dissolved in 75 ml of dry tetrahydrofuran and cooled to -78° C. in a dry ice-acetone bath under a nitrogen atmosphere, and was treated with 1.56 M n-butyl lithium (14.8 ml, 1 equivalent). The mixture was stirred for 30 minutes at -78° C. and then diethylphosphorochloridate (3.97 g) was added and stirring continued for 1 hour. The mixture was poured into saturated sodium chloride solution (60 ml) and extracted with ethyl acetate (three 40 ml portions). The extracts were combined and dried over anhydrous Na2SO4 and the solvent removed in vacuo. The residue was chromatographed on 125 g of silica gel eluted with ethyl acetate. Removal of solvent in vacuo followed by trituration with ether and drying yielding 4.72 g of the title compound, melting point 101°-103.5° C.

Workup

stirringstirring
waitcontinued for 1 hour
extractionextracted with ethyl acetate (three 40 ml portions)
dry with materialdried over anhydrous Na2SO4
customthe solvent removed in vacuo
customThe residue was chromatographed on 125 g of silica gel
washeluted with ethyl acetate
customRemoval of solvent in vacuo
customdrying

Sources & evidence

ORD record: ord-9dd90e5013a64d4999a77f7fb4f23b41
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04478749

Reaction notes

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