Trifluoroacetic acid → HCID 57253280, compound

HRID 893176Notes

Reaction equation

HRID 893176 reaction equation
[CH2:1]([CH:10]([CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1)[N:11]1[CH:14]([CH2:15][C:16]([O:18]CC2C=CC(OC)=CC=2)=[O:17])[CH:13]([CH:28]([O:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])[CH3:29])[C:12]1=[O:44])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.COC1C=CC=C(OC)C=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:45]([CH:10]([CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[N:11]1[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH:13]([CH:28]([O:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])[CH3:29])[C:12]1=[O:44])[C:46]1[CH:47]=[CH:48][C:49]([O:52][CH3:53])=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90251,3-DimethoxybenzeneHCID 57278229HCID 57278229, compound

Product 1

HCID 57253280HCID 57253280, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.2 g of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-p-methoxybenzyloxycarbonylmethyl-2-azetidinone was dissolved in 20 ml of dried methylene chloride, and 0.88 g of m-dimethoxybenzene and 2.5 ml of trifluoroacetic acid were added to the solution, followed by stirring at room temperature for 4 hours. The solvent was removed by distillation, and the resulting oily residue was subjected to silica gel chromatography to obtain 1.75 g of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-carboxymethyl-2-azetidinone.

Workup

  1. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-6b3308d622c8429fbe837617518ed187
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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