Triethylamine → HCID 88479256, compound

HRID 1613687Notes

Reaction equation

HRID 1613687 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][C:60]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])([CH3:62])[CH3:61])/[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:34]([CH2:38]I)[CH2:35][S:36](=[O:37])[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.Br.[OH:71][C:72]1[CH:73]=[C:74]2[C:79](=[CH:80][C:81]=1[OH:82])[CH:78]=[N:77][N:76]=[CH:75]2.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][C:60]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])([CH3:62])[CH3:61])/[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:34]([CH2:38][N:76]4[N:77]=[CH:78][C:79]5[C:74]([CH:73]=[C:72]([OH:71])[C:81](=[O:82])[CH:80]=5)=[CH:75]4)[CH2:35][S:36](=[O:37])[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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13180425HCID 13180425, compoundHCID 135760621HCID 135760621, compound

Product 1

HCID 88479256HCID 88479256, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-iodomethyl-3-cephem-4-carboxylate 1-oxide (IIa, 538 mg, 0.5 mmol), 6,7-dihydroxyphthalazine hydrobromide (158 mg, 0.65 mmol) and triethylamine (0.1 ml, 0.7 mmol) in DMF (1.5 ml) was stirred at room temperature for 3 hr. The reaction mixture was diluted with EtOAc (100 ml), washed with aqueous sodium thiosulfate, water, and aqueous sodium chloride, dried over magnesium sulfate and concentrated to yield 547 mg of a crude product, which was chromatographed on a silica gel column (7 g, 5% methanol in chloroform). The desired fractions were combined and concentrated to yield 532 mg (Yield 97%) of the title compound.

Workup

  1. washwashed with aqueous sodium thiosulfate, water, and aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto yield 547 mg of a crude product, which
  5. customwas chromatographed on a silica gel column (7 g, 5% methanol in chloroform)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-102f398175da4ad6b19842ab6669678b
Source dataset
uspto-grants-1993_03
Patent number
US05194433

Reaction notes

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