Citric Acid → HCID 178450878, compound

HRID 483049Notes

Reaction equation

HRID 483049 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]2([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]2)/[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.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:69][C@@H:70]1[C:88](=[O:89])[N:72]2[C:73]([C:85]([OH:87])=[O:86])=[C:74]([CH2:77][S:78][C:79]3[N:83]([NH2:84])[N:82]=[N:81][N:80]=3)[CH2:75][S:76][C@H:71]12.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(N(C)C)=O.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]2([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]2)/[C:27]([NH:69][C@@H:70]2[C:88](=[O:89])[N:72]3[C:73]([C:85]([OH:87])=[O:86])=[C:74]([CH2:77][S:78][C:79]4[N:83]([NH2:84])[N:82]=[N:81][N:80]=4)[CH2:75][S:76][C@H:71]23)=[O:28])[N:25]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 311Citric AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 19788589HCID 19788589, compound

Product 1

HCID 178450878HCID 178450878, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(1-tert-butoxycarbonylcyclopentyloxyimino)acetic acid (2.80 g, 4.7 mmol), 1-hydroxybenzotriazole (0.73 g, 5.4 mmol) and N,N'-dicyclohexylcarbodiimide (1.07 g, 5.17 mmol) in dimethylacetamide (26 ml) was stirred at room temperature for 2.5 hours. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (1.70 g, 5.17 mmol) and triethylamine (1.05 g, 10.3 mmol) in dimethylacetamide (13 ml) and water (1.7 ml), and the mixture was stirred at room temperature for 17 hours. The mixture was acidified with citric acid to pH 3.5 and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated. The residue was treated with isopropyl ether to give pale brown powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(1-tert-butoxycarbonylcyclopentyloxyimino)acetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (3.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was treated with isopropyl ether

Sources & evidence

ORD record
ord-4b18122817c340fd83454c80d72af40c
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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