2,6-Lutidine → HCID 54167408, compound

HRID 615121Notes

Reaction equation

HRID 615121 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([CH:25]([NH:36][CH:37]=O)[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:39])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O>C(Cl)Cl.C1C=CC=CC=1.C(OCC)(=O)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([CH:25]([N+:36]#[C-:37])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:39])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 14230822HCID 14230822, compound

Product 1

HCID 54167408HCID 54167408, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-formamidoacetate (2.70 g.) and 2,6-lutidine (11.4 ml.) in methylene chloride (16 ml.) was added dropwise phosphorus oxychloride (1.12 ml.) at 0° C. After stirring at the same temperature for 4.8 hours, the mixture was diluted with a mixture of benzene and ethyl acetate (120 ml.) (6:4 by volume), and washed successively with a chilled dilute aqueous solution of sodium chloride, a mixture of 10% phosphoric acid (75 ml.) and a saturated aqueous solution of sodium chloride, a dilute aqueous solution of sodium chloride, ice-water and a saturated aqueous solution of sodium chloride. Drying over magnesium sulfate and removal of the solvent left an oil (2.5 g.), which was chromatographed on silica gel (30 g.) with a mixed solvent of benzene and ethyl acetate (5:1 by volume) as an eluent to give an amorphous solid of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1 -azetidinyl]-2-isocyanoacetate.

Workup

  1. washwashed successively with a chilled dilute aqueous solution of sodium chloride
  2. additiona mixture of 10% phosphoric acid (75 ml.)
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil (2.5 g.), which
  5. customwas chromatographed on silica gel (30 g.) with a mixed solvent of benzene and ethyl acetate (5:1 by volume) as an eluent

Sources & evidence

ORD record
ord-167ca2c7b05040a0813a0f7f7041ea25
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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