Dicyclohexylcarbodiimide → HCID 131713478, compound

HRID 1904152Notes

Reaction equation

HRID 1904152 reaction equation
C(NC1SC=C(C(=NOCCN2CCOCC2)C(O)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[IH:40].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.C(OC[C:67]1[CH2:68][S:69][C@@H:70]2[CH:90](N)[C:89](=[O:92])[N:71]2[C:72]=1[C:73]([O:75]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:74])(=O)C>CN(C)C=O>[IH:40].[S:69]1[C@@H:70]2[CH2:90][C:89](=[O:92])[N:71]2[C:72]([C:73]([OH:75])=[O:74])=[CH:67][CH2:68]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 31273118820-83-2HCID 12884459HCID 12884459, compoundHCID 54498501HCID 54498501, compound

Product 1

HCID 131713478HCID 131713478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g of the product of Step A, 0.38 g of pyridine hydroiodide, 0.63 g of dicyclohexylcarbodiimide, 0.60 g of benzhydryl 3-acetoxymethyl-7-amino-ceph-3-eme-4-carboxylate and 5 ml of anhydrous dimethylformamide was stirred at room temperature for 30 minutes and was vacuum filtered to remove dicyclohexylurea. 100 ml of ether were added to the filtrate and the mixture was stirred for 10 minutes and was vacuum filtered. The product was rinsed with ether and was chromatographed over silica gel. Elution with a 7-1 ethyl acetate-ethanol mixture yielded 0.524 g of the syn isomer of benzhydryl 3-acetoxymethyl-7-[2-2tritylamino-4-thiazolyl)-2-(2-morpholinoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate hydroiodide melting at 167° C. (decomposition).

Workup

  1. filtrationfiltered
  2. customto remove dicyclohexylurea
  3. addition100 ml of ether were added to the filtrate
  4. filtrationfiltered
  5. washThe product was rinsed with ether
  6. customwas chromatographed over silica gel
  7. washElution with a 7-1 ethyl acetate-ethanol mixture

Sources & evidence

ORD record
ord-31c3df6b5a46432d843d10570b5129a2
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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