Dicyclohexylcarbodiimide → 3-[(Acetyloxy)methyl]-7-[[3-ethoxy-1,3-dioxo-2-(2,3-dihydro-5-benzofuranyl)propyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-(acetyloxy)benzyl ester

HRID 904025Notes

Reaction equation

HRID 904025 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:32])[CH:10]2[NH:14][C:15](=[O:31])[CH:16]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][CH2:28][CH2:27][C:26]=3[CH:30]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]=1[C:33]([OH:35])=[O:34])(=[O:3])[CH3:2].[Na].[C:37]([O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45]O)=[CH:43][CH:42]=1)(=[O:39])[CH3:38].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:37]([O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][O:34][C:33]([C:7]2[N:8]3[CH:11]([S:12][CH2:13][C:6]=2[CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:10]([NH:14][C:15](=[O:31])[CH:16]([C:22]2[CH:23]=[CH:24][C:25]4[O:29][CH2:28][CH2:27][C:26]=4[CH:30]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:9]3=[O:32])=[O:35])=[CH:43][CH:42]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 959064-Acetoxybenzyl alcoholHCID 5360545SodiumHCID 233358303-[(Acetyloxy)methyl]-7-[[3-ethoxy-1,3-dioxo-2-(2,3-dihydro-5-benzofuranyl)-propyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 537929593-[(Acetyloxy)methyl]-7-[[3-ethoxy-1,3-dioxo-2-(2,3-dihydro-5-benzofuranyl)propyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-(acetyloxy)benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 6 mmole of 3-[(acetyloxy)methyl]-7-[[3-ethoxy-1,3-dioxo-2-(2,3-dihydro-5-benzofuranyl)-propyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, sodium salt in 40 ml of dimethylformamide (DMF) is added 2 equivalents of p-(acetyloxy)-benzyl alcohol. The mixture is cooled to 0° C. after which 6.8 mM of dicyclohexylcarbodiimide in 10 ml of DMF is added dropwise with stirring. The mixture is stirred at 0° C. for 1 hour and an addition 4 hours at room temperature. 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 the title compound.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is stirred at 0° C. for 1 hour
  3. additionan addition 4 hours at room temperature
  4. customDicyclohexylurea is removed by filtration
  5. additionThe filtrate is diluted with chloroform
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3d84ee65bf7e49b49f48e928d45428b9
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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