Formaldehyde → HCID 19748777, compound

HRID 2118786Notes

Reaction equation

HRID 2118786 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 mmol) azetidinone from Step A, 26.3 mg paraformaldehyd 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 evaporated 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 evaporated in vacuo

Sources & evidence

ORD record
ord-3e2d9619e3fc441196ec64a946da6b65
Source dataset
uspto-grants-1987_07
Patent number
US04680391

Reaction notes

Loading…