Pyridine → HCID 178423843, compound

HRID 973870Notes

Reaction equation

HRID 973870 reaction equation
[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)/[C:27]([O-:29])=O)[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].CS(Cl)(=O)=O.[NH2:57][C@@H:58]1[C:89](=[O:90])[N:60]2[C:61]([C:73]([O:75][CH:76]([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=3)=[O:74])=[C:62](/[CH:65]=[C:66]3\[CH:67]=[C:68]([CH3:72])[C:69](=[O:71])[O:70]\3)[CH2:63][S:64][C@H:59]12.N1C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH3:72][C:68]1[C:69](=[O:71])[O:70]/[C:66](=[CH:65]/[C:62]2[CH2:63][S:64][C@@H:59]3[C@H:58]([NH:57][C:27](=[O:29])/[C:26](=[N:30]\[O:31][C:32]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)/[C:24]4[N:25]=[C:21]([NH:20][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)[S:22][CH:23]=4)[C:89](=[O:90])[N:60]3[C:61]=2[C:73]([O:75][CH:76]([C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[O:74])/[CH:67]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23714200sodium (2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetateHCID 67923953diphenylmethyl 7beta-amino-3-(E-2,5-dihydro-3-methyl-2-oxofuran-5-ylidenemethyl)ceph-3-em-4-carboxylate

Product 1

HCID 178423843HCID 178423843, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

Sodium 2-(2-triphenylmethylaminothiazol-4-yl)2-Z-triphenylmethoxyiminoacetate (0.832 g), in dry DMF (2 mls) was cooled to ca -50° C. under argon and treated with methanesulphonyl chloride (0.093 mls). The solution was allowed to warm to -15° C. over 30mins and then treated with a solution of diphenylmethyl 7β-amino-3-(E-2,5-dihydro-3-methyl-2-oxofuran-5-ylidenemethyl)ceph-3-em-4-carboxylate (0.474 g) and pyridine (0.096 mls) in DMF (3 mls). The reaction was allowed to warm to room temperature over 1h., diluted with ethyl acetate and washed with water (3×), brine and dried. After removal of solvent, flash chromatography on silica gel eluting with 30, 40% ethyl acetate/hexane, gave the title compound as a foam, (0.444 g, 39%), νmax (CH2Cl2) 3375, 1780 (shoulder), 1760, 1720, 1680 and 1500cm-1 ; δH (CDCl3) 1.88 (3H,s), 3.37 (2H,ABq, J17.6Hz), 5.14 (1H,d,J5.1Hz), 6.10 (1H,dd,J5.1,8.8Hz), 6.44 (1H,s), 6.48 (1H,s) 6.77 (1H,br.s, exch.), 6.98 (1H,s), 7.00 (1H,s) and 7.2-7.4 (40H,m); [mass spectrum: +ve ion (NOBA) MH+, 1128].

Workup

  1. temperatureto warm to room temperature over 1h.
  2. washwashed with water (3×), brine
  3. customdried
  4. customAfter removal of solvent, flash chromatography on silica gel eluting with 30, 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d048aa5349164c9aa466d6dfeb8ca40b
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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