Dicyclohexylcarbodiimide → 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-pivalyloxybenzyl ester

HRID 442361Notes

Reaction equation

HRID 442361 reaction equation
Cl.[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:29])[CH:11]2[NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:20][CH:19]=2)[C:8]=1[C:30]([OH:32])=[O:31])(=[O:4])[CH3:3].[C:33]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]O)=[CH:42][CH:41]=1)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:33]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:31][C:30]([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]([NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:22][CH:23]=2)[C:10]3=[O:29])=[O:32])=[CH:42][CH:41]=1)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 116009134-(Hydroxymethyl)phenyl pivalateHCID 867350423-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride

Product 1

HCID 543805993-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]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 solution of 1.8 of 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride in 25 ml of dimethyl formamide is added 0.78 g of p-pivalyloxybenzyl alcohol followed by cooling to 0° C after which 3.7 mole of dicyclohexylcarbodiimide in 7.5 ml of dimethyl formamide is added dropwise with stirring. The reaction mixture is stirred for 1 hour at 0° C. and for an additional 4 hours at room temperature. The formed dicyclohexylurea is removed by filtration. The filtrate is diluted with chloroform and washed with water. The organic layer is then dried over magnesium sulfate filtered and evaporated in vacuo to give an oil which is triturated with ether to give 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]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 reaction mixture is stirred for 1 hour at 0° C. and for an additional 4 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 materialThe organic layer is then dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give an oil which
  10. customis triturated with ether

Sources & evidence

ORD record
ord-49a212b854ec49b7860df88f2807d344
Source dataset
uspto-grants-1977_08
Patent number
US04045438

Reaction notes

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