Dicyclohexylcarbodiimide → HCID 13060635, compound

HRID 1973075Notes

Reaction equation

HRID 1973075 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[CH:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[N:31]([CH3:32])[N:30]=[N:29][N:28]=2)[CH:20](N)[C:19]3=[O:34])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:32][N:31]1[C:27]([S:26][CH2:25][C:24]2[CH2:23][S:22][CH:21]3[N:18]([C:19](=[O:34])[CH2:20]3)[C:17]=2[C:15]([O:14][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:16])=[N:28][N:29]=[N:30]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 12873515HCID 12873515, compound

Product 1

HCID 13060635HCID 13060635, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of part a and 7-amino-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid diphenylmethyl ester are dissolved in 650 ml. of absolute tetrahydrofuran and the solution is cooled to 0°. At this temperature, a solution of 7.3 gms. of dicyclohexylcarbodiimide in 60 ml. of absolute tetrahydrofuran is added dropwise over a period of about 20 minutes. The mixture is stirred at 0° for two hours and an additional two hours at room temperature. The dicyclohexylurea which precipitates is removed by filtration. The filtrate is concentrated in vacuum. The residue is dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution, then with water and dried with magnesium sulfate. After filtration, the filtrate is left overnight in the refrigerator. The reaction product crystallizes. On filtration 12.2 gms. of 7β-[[[[[(4-methoxyphenyl)methoxy]carbonyl]amino]-2-thienyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]-methyl]-8 -oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester are obtained, m.p. 126° (dec.). The filtrate is evaporated to dryness. Treatment with ethyl acetate yields a second crop of 2.6 gms. A third crop of 2.6 gms. is obtained when the filtrate is evaporated, dissolved in a small amount of ethyl acetate, precipitated with petroleum ether and again treated with ethyl acetate.

Workup

  1. customThe dicyclohexylurea which precipitates
  2. customis removed by filtration
  3. concentrationThe filtrate is concentrated in vacuum
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialwith water and dried with magnesium sulfate
  7. filtrationAfter filtration
  8. waitthe filtrate is left overnight in the refrigerator
  9. customThe reaction product crystallizes
  10. filtrationOn filtration 12.2 gms

Sources & evidence

ORD record
ord-4daabbe3e3d5414089d48a48551c0156
Source dataset
uspto-grants-1976_12
Patent number
US03996219

Reaction notes

Loading…