Dicyclohexylcarbodiimide → HCID 21426452, compound

HRID 258697Notes

Reaction equation

HRID 258697 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH2:14])[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[S:38]([C:42]1[N:43]([CH2:47][C:48](O)=[O:49])[CH:44]=[CH:45][N:46]=1)([CH3:41])(=[O:40])=[O:39]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH:14][C:48](=[O:49])[CH2:47][N:43]2[CH:44]=[CH:45][N:46]=[C:42]2[S:38]([CH3:41])(=[O:40])=[O:39])[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800, compoundHCID 21426444HCID 21426444, compound

Product 1

HCID 21426452HCID 21426452, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Acetoxymethyl-7-amino-2-(tertiary butoxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (5.65 g.) and dicyclohexylcarbodiimide (3.90 g.) are added to a solution of (2-mesyl-imidazol-1-yl)-acetic acid (3.53 g) in dimethylformamide (30 cc.). The reagents are left in contact for 3 days at a temperature of about 20° C., and then the solid is filtered off. The filtrate is taken up in ethyl acetate (150 cc.) and washed successively with a saturated aqueous solution of sodium bicarbonate, with 0.5 N hydrochloric acid and then with water. The organic extracts are dried over sodium sulphate and then treated with decolorising charcoal. After concentration to dryness under reduced pressure (20 mm.Hg), the crystalline residue is washed with isopropyl ether (70 cc.). 3-Acetoxymethyl-2-(tertiary butoxycarbonyl)-7-[(2-mesyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (7.4 g.), which melts at 164° C., is thus obtained.

Workup

  1. filtrationthe solid is filtered off
  2. washwashed successively with a saturated aqueous solution of sodium bicarbonate, with 0.5 N hydrochloric acid
  3. dry with materialThe organic extracts are dried over sodium sulphate
  4. additiontreated with decolorising charcoal
  5. concentrationAfter concentration to dryness under reduced pressure (20 mm.Hg)
  6. washthe crystalline residue is washed with isopropyl ether (70 cc.)

Sources & evidence

ORD record
ord-1762eced7ebc4653a84b89e522f6d056
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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