Dicyclohexylcarbodiimide → 3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-pivalyloxybenzyl ester

HRID 1604915Notes

Reaction equation

HRID 1604915 reaction equation
[Na+].[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:16])[CH:11]2[NH2:15])[C:8]=1[C:17]([O-:19])=[O:18])(=[O:4])[CH3:3].[C:20]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]O)=[CH:29][CH:28]=1)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:20]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:18][C:17]([C:8]2[N:9]3[CH:12]([S:13][CH2:14][C:7]=2[CH2:6][O:5][C:2](=[O:4])[CH3:3])[CH:11]([NH2:15])[C:10]3=[O:16])=[O:19])=[CH:29][CH:28]=1)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 116009134-(Hydroxymethyl)phenyl pivalateHCID 236640673-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

Product 1

HCID 540797063-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-pivalyloxybenzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 6.6 mM of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt in 35 ml of dimethyl formamide (DMF) is added 2 equivalents of p-pivalyloxybenzyl alcohol followed by cooling to 0°C after which 7.2 mM of dicyclohexylcarbodiimide in 7.5 ml of DMF is added dropwise with stirring. The mixture is stirred at 0°C for one hour and an additional four hours at room temperature. The formed dicyclohexylurea is removed by filtration. The filtrate is diluted with chloroform, washed with water, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-pivalyloxybenzyl ester.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is stirred at 0°C for one hour and an additional four hours at room temperature
  3. customThe formed dicyclohexylurea is removed by filtration
  4. additionThe filtrate is diluted with chloroform
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ca81005533742358440d99c81a695cf
Source dataset
uspto-grants-1976_04
Patent number
US03948904

Reaction notes

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