Sodium Chloride → HCID 86739724, compound

HRID 1632943Notes

Reaction equation

HRID 1632943 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.[P:20](Cl)(=[O:25])([O:23][CH3:24])[O:21][CH3:22].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:12][C@H:11]1[N:10]([P:20](=[O:25])([O:23][CH3:24])[O:21][CH3:22])[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

7

Reactant 4

HCID 5234Sodium ChlorideHCID 101863Phosphorochloridic acid, dimethyl esterHCID 57285608rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamateHCID 178418339Butyllithium

Product 1

HCID 86739724HCID 86739724, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S-cis)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-azetidinone (918 mg) dissolved in dry tetrahydrofuran (25 ml) was cooled to -78° C. under an inert atmosphere and 1.56 M n-butyl lithium (3 ml) was added while stirring. After thirty minutes dimethyl phosphorochloridate (3.0 ml) was added and the mixture was stirred at -78° C. for 2 hours. Saturated sodium chloride solution (20 ml) was added and the mixture allowed to warm to room temperature and extracted three times with 30 ml ethyl acetate portions. The combined extracts were dried (Na2SO4) and solvent was removed in vacuo yielding an oil. Chromatography of the oil dissolved in 4 ml of ethyl acetate on a 34 g silica gel column eluting with ethyl acetate yielded 875 mg of the title compound.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at -78° C. for 2 hours
  3. extractionextracted three times with 30 ml ethyl acetate portions
  4. dry with materialThe combined extracts were dried (Na2SO4) and solvent
  5. customwas removed in vacuo
  6. customyielding an oil
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5a71a18867ce4f2a91900836a3c043c3
Source dataset
uspto-grants-1984_10
Patent number
US04478749

Reaction notes

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