Urea → HCID 178520132, compound

HRID 1461166Notes

Reaction equation

HRID 1461166 reaction equation
[Br:1][CH2:2][C:3](=[O:40])[CH2:4][C:5]([NH:7][CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:12](/[CH:15]=[CH:16]\[C:17]3[N:18]=[N:19][S:20][CH:21]=3)[CH2:13][S:14][C@H:9]12)=[O:6].[N:41]([O-])=[O:42].[Na+].NC(N)=O>C(Cl)Cl.C(O)(=O)C>[Br:1][CH2:2][C:3](=[O:40])[C:4](=[N:41][OH:42])[C:5]([NH:7][CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[C:12](/[CH:15]=[CH:16]\[C:17]3[N:18]=[N:19][S:20][CH:21]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 1176UreaHCID 15010083HCID 15010083, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178520132HCID 178520132, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

A methylene chloride-acetic acid (20 ml-10 ml) solution of diphenylmethyl 7-(4-bromoacetoacetamido)-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (2.22 g, 3.4 mmol) was cooled from -7° C. to -5° C. and an aqueous solution (2 ml) of sodium nitrite (0.32 g, 4.6 mmol) was added in portions. After its dropwise addition the mixture was stirred for 30 minutes, then urea (0.3 g) was added and the temperature of the reaction solution was returned to toom temperature. The reaction mixture was extracted with methylene chloride, then washed with water (40 ml×2) and then dried over magnesium sulfate. When the solvent was distilled off, diphenylmethyl 7-(4-bromo-2-hydroxyiminoacetoacetamido)-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (1.85 g) was obtained as a light yellow powder compound.

Workup

  1. additionAfter its dropwise addition the mixture
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. washwashed with water (40 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. distillationWhen the solvent was distilled off

Sources & evidence

ORD record
ord-e34aa82cbfea4fd7ac952197a91b0059
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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