Hydrochloric Acid → 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-(5-indanyloxycarbonyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1111757Notes

Reaction equation

HRID 1111757 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:31])[CH:10]2[NH:14][C:15](=[O:30])[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]=[N+:28]=[N-:29])=[CH:22][CH:21]=2)[C:17]([OH:19])=[O:18])[C:7]=1[C:32]([OH:34])=[O:33])(=[O:3])[CH3:2].Cl.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:51]1[C:59]2[C:54](=[CH:55][C:56](O)=[CH:57][CH:58]=2)[CH2:53][CH2:52]1>O1CCOCC1>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:31])[CH:10]2[NH:14][C:15](=[O:30])[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]=[N+:28]=[N-:29])=[CH:22][CH:21]=2)[C:17]([O:19][C:56]2[CH:55]=[C:54]3[C:59](=[CH:58][CH:57]=2)[CH2:51][CH2:52][CH2:53]3)=[O:18])[C:7]=1[C:32]([OH:34])=[O:33])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 151185-IndanolHCID 227677693-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 227677673-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-(5-indanyloxycarbonyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 25.3 m mole of 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in 35 ml dioxane is added 6N hydrochloric acid to give a pH of 2.5. Then 24.1 m moles N,N'-dicyclohexylcarbodiimide in 35 ml dioxane is added and the mixture is stirred at room temperature for 15 to 20 minutes followed by the addition of 24.1 m moles of 5-indanol. The mixture is stirred for 4 hours. The formed N,N'-dicyclohexylurea is removed by filtration and the filtrate is extracted 3 times with methyl isobutyl ketone. The organic extract is washed with water, dried over magnesium sulfate and concentrated to dryness in vacuo to yield 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-(5-indanyloxycarbonyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. customto give a pH of 2.5
  2. stirringThe mixture is stirred for 4 hours
  3. customThe formed N,N'-dicyclohexylurea is removed by filtration
  4. extractionthe filtrate is extracted 3 times with methyl isobutyl ketone
  5. extractionThe organic extract
  6. washis washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-7713987e41464c6e8054645c957e65cf
Source dataset
uspto-grants-1978_10
Patent number
US04118562

Reaction notes

Loading…