Chlorotrimethylsilane → HCID 178460196, compound

HRID 1085227Notes

Reaction equation

HRID 1085227 reaction equation
[OH:1][C:2]1[C:3](=[O:15])[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([OH:14])=O.C[Si](Cl)(C)C.S(Cl)(Cl)=O.[NH2:25][CH2:26][C:27]1[CH2:28][S:29][C@@H:30]2[CH:37]([NH:38][C:39](=[O:55])/[C:40](/[C:49]3[N:50]=[C:51]([NH2:54])[S:52][CH:53]=3)=[N:41]\[O:42][C:43]([C:46]([OH:48])=[O:47])([CH3:45])[CH3:44])[C:36](=[O:56])[N:31]2[C:32]=1[C:33]([OH:35])=[O:34]>C(Cl)(Cl)Cl.CO.O.C(N(CC)CC)C>[NH2:54][C:51]1[S:52][CH:53]=[C:49](/[C:40](=[N:41]/[O:42][C:43]([C:46]([OH:48])=[O:47])([CH3:45])[CH3:44])/[C:39]([NH:38][CH:37]2[C:36](=[O:56])[N:31]3[C:32]([C:33]([OH:35])=[O:34])=[C:27]([CH2:26][NH:25][C:12]([C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:5]=4[N:4]=[C:3]([OH:15])[C:2]([OH:1])=[CH:11]5)=[O:14])[CH2:28][S:29][C@H:30]23)=[O:55])[N:50]=1

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24386Thionyl ChlorideHCID 20060980HCID 20060980, compoundHCID 88403825HCID 88403825, compound

Product 1

HCID 178460196HCID 178460196, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent3×

Conditions

Temperature
60 °C

Procedure

To a solution of 3-hydroxy-8-carboxy-2(1H)-quinolinone (160 mg) in chloroform (15 ml) was added triethylamine (0.62 ml) and speedily trimethylsilyl chloride (0.57 ml). The mixture was heated to 60° C. for 4 hours, cooled to 0° C. and treated with triethylamine (0.114 ml) and thionyl chloride (0.06 ml), whereupon the resultant solution was stirred for 2 hours at 0° C. and at room temperature for 30 minutes. This solution was added to 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]ceph-3-em-4-carboxylic acid (360 mg) in methanol (30 ml) containing triethylamine (0.42 ml) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C., stirred for 30 minutes at room temperature, diluted with water, acidified to pH2, concentrated, and purified by chromatography (HP20SS resin eluting with methanol/water/acetic acid) to give the title compound (85 mg); NMR (DMSO-d6 /CD3COOD/CF3COOD) 1.50(s,6H); 3.55(m,2H); 4.40(m,2H); 5.1(d,1H); 5.75(d,1H); 7.00-7.25(,3H); 7.6(d,1H); 7.80(d,1H).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred for 30 minutes at 0° C.
  3. stirringstirred for 30 minutes at room temperature
  4. concentrationconcentrated
  5. custompurified by chromatography (HP20SS resin eluting with methanol/water/acetic acid)

Sources & evidence

ORD record
ord-9d0e60f580314d5ea1d5b674cb5cb333
Source dataset
uspto-grants-1991_04
Patent number
US05008259

Reaction notes

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