Acetic Acid → HCID 88473887, compound

HRID 2165289Notes

Reaction equation

HRID 2165289 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:46]/[O:47][C:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])([CH3:50])[CH3:49])/[C:27]([NH:29][CH:30]2[C:44](=[O:45])[N:32]3[C:33]([C:41]([OH:43])=[O:42])=[C:34]([CH2:37]SC#N)[CH2:35][S:36][C@H:31]23)=[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.[CH:58]([NH:61]C(C)C)(C)[CH3:59].C1(C)C=CC=CC=1.C(O)(=O)C>CC#N.CCOCC>[CH2:58]([NH:61][CH2:37][C:34]1[CH2:35][S:36][C@@H:31]2[CH:30]([NH:29][C:27](=[O:28])/[C:26](/[C:24]3[N:25]=[C:21]([NH:20][C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[S:22][CH:23]=3)=[N:46]\[O:47][C:48]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])([CH3:49])[CH3:50])[C:44](=[O:45])[N:32]2[C:33]=1[C:41]([OH:43])=[O:42])[CH3:59]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7912DiisopropylamineHCID 88474285HCID 88474285, compound

Product 1

HCID 88473887HCID 88473887, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

7-[2-(2-tritylaminothiazol-4-yl)-2((Z)-1-t-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-cyanothiomethylceph-3-em-4-carboxylic acid (10 g) was dissolved in CH3CN (100 ml) and treated, quickly, dropwise at room temperature, with a mixture of 1,3,5-THT (4.2 g, 4.6 ml) and diisopropylamine (3.1 g, 4.1 ml). After 15 min at room temperature the solution was poured into a mixture of toluene (500 ml) and glacial acetic acid (50 ml) and extracted several times with brine. The organic phase was dried over MgSO4, filtered through celite and evaporated to give a foam. Trituration of the foam with ether gave 3-ethylaminomethyl-7-[2-(2-tritylamino-thiazol-4-yl)-2((Z)-1-t-butoxycarbonyl-1-methylethoxy-imino)-acetamido]ceph-3-em-4-carboxylic acid as a granular solid (9.08 g, 92% yield) NMR (200 MHzd6DMSO+CD3COOD): 1.17(t,3H); 1.32(s,9H); 1.39(s,3H); 1.40(s,3H); 2.96 (q,2H); 3.54(d,1H); 3.59(d,1H); 3.65(d,1H); 3.86(d,1H); 5.08(d,1H); 5.69(d,1H); 6.68(s,1H); 7.1-7.4(m,15H).

Workup

  1. additiontreated
  2. extractionextracted several times with brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered through celite
  5. customevaporated
  6. customto give a foam

Sources & evidence

ORD record
ord-6a4a502d989a46858a925e50e0eded93
Source dataset
uspto-grants-1990_07
Patent number
US04939250

Reaction notes

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