HCID 14488848, compound → HCID 76083593, compound

HRID 2082613Notes

Reaction equation

HRID 2082613 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:17])[CH3:16])[C:8]([O-:10])=[O:9])(=[O:3])[CH3:2].[Na+].[CH3:19][C:20]([O:23][C:24]([C:26]1[N:27]2[C@H:30]([S:31][CH2:32][C:33]=1[CH2:34]I)[C@H:29]([NH:36][C:37](=[O:46])[CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:28]2=[O:47])=[O:25])([CH3:22])[CH3:21].CCCCCC.CCOC(C)=O>CN(C=O)C>[CH3:22][C:20]([O:23][C:24]([C:26]1[N:27]2[CH:30]([S:31][CH2:32][C:33]=1[CH2:34][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([O:14][C:15](=[O:17])[CH3:16])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=1)[CH:29]([NH:36][C:37](=[O:46])[CH2:38][O:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:28]2=[O:47])=[O:25])([CH3:19])[CH3:21]

Participants

5

Reactant 3

HCID 14488848HCID 14488848, compoundHCID 21226206Ethyl acetate hexaneHCID 23716498HCID 23716498, compound

Product 1

HCID 76083593HCID 76083593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

By following the procedures and conditions described in Example 4, 2.33 g (8.95 mmol) of sodium 3,4-diacetoxybenzoate in 100 mL of DMF added to 4.75 g (8.95 mmol) of (6R-trans)-3-(iodomethyl)-8-oxo-7-[(phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1,1-dimethylethyl ester in 50 mL of DMF, followed by stirring for 2 hours, gave 3.36 g (58.5%) of a cream colored solid after silica gel chromatography (6:4 hexane/EtOAc).

Workup

  1. customgave 3.36 g (58.5%) of a cream

Sources & evidence

ORD record
ord-352f0048a98e448ea95cedf016e241c2
Source dataset
uspto-grants-1993_02
Patent number
US05189157

Reaction notes

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