Methanol → HCID 88661271, compound

HRID 980956Notes

Reaction equation

HRID 980956 reaction equation
C([S:4][C:5]([S:26]C(=O)C)=[C:6]([N:20]1[CH:23](Cl)[CH2:22][C:21]1=[O:25])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:8])(=O)C.CO.CN>C(Cl)Cl.C(N(CC)CC)C>[S:4]=[C:5]1[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[N:20]2[C:21](=[O:25])[CH2:22][C@H:23]2[S:26]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 20220771HCID 20220771, compound

Product 1

HCID 88661271HCID 88661271, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1(b), a carbon tetrachloride solution containing an equimolar amount of chlorine was added to a solution of p-nitrobenzyl 2-[bis(acetylthio)methylidene]-2-(4-methylthio-2-azetidinon-1-yl)acetate (144 mg, 0.306 mmole) in methylene chloride (2 ml) to give p-nitrobenzyl 2-[bis(acetylthio)methylidene]-2-(4chloro-2-azetidinon-1-yl)acetate. This crude 4-chloroazetidinone derivative was dissolved in methylene chloride (3 ml) and triethylamine (43 μl), and then 135 μl of a 30% methanol solution of methylamine were added thereto, after which the mixture was stirred for 15 minutes. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent:ethyl acetate) to afford 60 mg of the desired compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-d8a83234d92941d4975cf6aa33990ca1
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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