Formaldehyde → HCID 19748777, compound

HRID 484041Notes

Reaction equation

HRID 484041 reaction equation
[CH2:1]([CH:4]1[CH:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[NH:6][C:5]1=[O:18])[CH2:2][CH3:3].C=O.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]([O:30][C:31](=O)C)(=[O:29])[CH3:28]>O1CCCC1.N1C=CC=CC=1>[C:27]([O:30][CH2:31][N:6]1[CH:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:18])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 7918Acetic AnhydrideHCID 10796Cesium carbonateHCID 19748757HCID 19748757, compound

Product 1

HCID 19748777HCID 19748777, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 273 mg (0.94 mmole) azetidinone from Step A, 26.3 mg paraformaldehyde and 178 mg (0.56 mmole) cesium carbonate was stirred in 20 ml dry tetrahydrofuran at ambient temperature 16.5 hours under nitrogen. A mixture of 430 μl pyridine and 2.56 ml acetic anhydride was added to the reaction mixture and the stirring continued 5 more hours. The solvents were removed in vacuo to give 604 mg crude product which was chromatographed on a silica gel flash column in hexane-ethyl acetate 3/1. This gave 102 mg (30%) of 1-acetoxymethyl-4-p-nitrophenylthio-3-n-propylazetidin-2-one.

Workup

  1. additionwas added to the reaction mixture
  2. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-8a73a1c796214e69ad9797ddfa5e730b
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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