Sodium Chloride → HCID 13366924, compound

HRID 1632937Notes

Reaction equation

HRID 1632937 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:15][NH:14][C:13]1=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(CC)C.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[P:29](=O)([O-:33])[O:30][CH2:31][CH3:32].[Cl-].[Na+]>O1CCCC1>[CH2:31]([O:30][P:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:23]=1)([N:14]1[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]1=[O:16])=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 12834623Benzyl (2-oxoazetidin-3-yl)carbamateHCID 86233611HCID 86233611, compoundHCID 178418400CID 53628100

Product 1

HCID 13366924HCID 13366924, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxycarbonylamino-2-azetidinone (5.0 g) in dry tetrahydrofuran (125 ml), cooled to -78° C., was added sec-butyl lithium (18.5 ml) and the mixture was stirred for 5 minutes. Ethyl chlorophenylphosphonate (4.71 g) was added and the mixture was stirred for 1 hour at -78° C. followed by the addition of 125 ml of saturated sodium chloride solution. The mixture was then extracted twice with 125 ml portions of ethyl acetate and the extracts were combined, dried over anhydrous sodium sulfate and the solvent removed in vacuo yielding the crude product as a foam. The crude product was purified by chromatography on silica gel (750 g), eluting with dichloromethane:ethyl acetate (1:1) followed by ethyl acetate. The ethyl acetate fractions were stripped and the residue triturated with ether to yield 4.94 g of product.

Workup

  1. stirringthe mixture was stirred for 1 hour at -78° C.
  2. extractionThe mixture was then extracted twice with 125 ml portions of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed in vacuo
  5. customyielding the crude product as a foam
  6. customThe crude product was purified by chromatography on silica gel (750 g)
  7. washeluting with dichloromethane:ethyl acetate (1:1)
  8. customthe residue triturated with ether

Sources & evidence

ORD record
ord-87b604cc0b97427c814f2ae5240a2609
Source dataset
uspto-grants-1984_10
Patent number
US04478749

Reaction notes

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