Acetic Acid → HCID 178452985, compound

HRID 1707446Notes

Reaction equation

HRID 1707446 reaction equation
[C:1]([S:9][CH2:10][S:11][C:12]1[N:13]=[N:14][NH:15][CH:16]=1)(=O)[C:2]1C=CC=CC=1.[CH3:17][O-:18].[Na+].C1(C(OC([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39]CC=2OS(C)(=O)=O)=O)C2C=CC=CC=2)C=CC=CC=1.[C:88](O)(=O)[CH3:89].[CH3:92][OH:93]>CN(C)C=O.O>[C:50]1([CH:17]([O:18][C:92]([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:78])([CH3:80])[CH3:79])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39][CH2:2][C:1]=2[S:9][CH2:10][S:11][C:12]2[N:13]=[N:14][NH:15][CH:16]=2)=[O:93])[C:89]2[CH:88]=[CH:72][CH:68]=[CH:46][CH:45]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 10260338benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-3-methylsulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 10942334Sodium MethoxideHCID 178526204HCID 178526204, compound

Product 1

HCID 178452985HCID 178452985, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-benzoylthiomethylthio-1,2,3-triazole (150 mg: 0.60 mMol.) in dimethylformamide (3 ml) at -60° C. is added a solution of sodium methoxide in methanol (1.26N: 0.95 ml), and the mixture is stirred for 80 minutes at -50° to -60° C. To the mixture at -70° C. is added a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester (485 mg: 0.5 mMol.) in dimethylformamide (2 ml) and the mixture is stirred at -70° C. for 20 minutes. The reaction mixture is mixed with acetic acid (0.1 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. The residue is crystallized from toluene to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3 -cephem-4-carboxylic acid diphenylmethyl ester (227 mg) as colorless crystals. Yield: 44%.

Workup

  1. stirringthe mixture is stirred at -70° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized from toluene

Sources & evidence

ORD record
ord-d687218b1c8543588c2e7fe107660093
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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