Hydrochloric Acid → HCID 131711504, compound

HRID 2049156Notes

Reaction equation

HRID 2049156 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH:33]=[CH2:34])[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:50][C:51]([O:53][CH2:54][C:55]1[CH2:64][S:63][C@@H:58]2[C@H:59]([NH2:62])[C:60](=[O:61])[N:57]2[C:56]=1[C:65]([OH:67])=[O:66])=[O:52].Cl>O.C(N(CC)CC)C.C(Cl)Cl>[C:51]([O:53][CH2:54][C:55]1[CH2:64][S:63][C@@H:58]2[CH:59]([NH:62][C:27](=[O:28])[C:26]([C:24]3[N:25]=[C:21]([NH:20][C:1]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[S:22][CH:23]=3)=[N:30][O:31][CH2:32][CH:33]=[CH2:34])[C:60](=[O:61])[N:57]2[C:56]=1[C:65]([OH:67])=[O:66])(=[O:52])[CH3:50]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 4413287-Aminocephalosporanic acidHCID 53877541HCID 53877541, compound

Product 1

HCID 131711504HCID 131711504, compoundYield 168.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 470 mg of the product of Step C, 5 ml of methylene chloride and 130 ml of dicyclohexylcarbodiimide was rinsed with a little methylene chloride and the mixture was stirred for an hour at room temperature. The mixture was vacuum filtered to remove the dicyclohexylurea formed and the filtrate was cooled. A solution of 136 mg of 7-amino-cephalosporanic acid, 2.4 ml of methylene chloride and 0.14 ml of triethylamine was added to the filtrate under an inert atmosphere and the mixture sat for 11/2 hours at room temperature. 2 ml of 1 N hydrochloric acid and water were added thereto and the mixture was stirred and decanted. The organic phase was washed with water, dried and evaporated to dryness to obtain 610 mg of raw 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-propenyl) oxyiminoacetamido]-ceph-3-eme-4-carboxylic acid with a syn configuration.

Workup

  1. washwas rinsed with a little methylene chloride
  2. filtrationfiltered
  3. customto remove the dicyclohexylurea
  4. customformed
  5. temperaturethe filtrate was cooled
  6. custom2 hours
  7. customat room temperature
  8. stirringthe mixture was stirred
  9. customdecanted
  10. washThe organic phase was washed with water
  11. customdried
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-7830c38eec3043a0ab0864039f5ff112
Source dataset
uspto-grants-1980_04
Patent number
US04196205

Reaction notes

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