Hydrochloric Acid → HCID 88179846, compound

HRID 992700Notes

Reaction equation

HRID 992700 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:60]/[O:61][C:62]([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)/[C:27]([NH:29][C@@H:30]2[C:58](=[O:59])[N:32]3[C:33]([C:42]([O:44][CH:45]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[O:43])=[C:34](OS(C)(=O)=O)[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.[SH:81][C:82]1[CH:87]=[CH:86][N:85]=[CH:84][CH:83]=1.C(N(CC)C(C)C)(C)C.Cl>CN(C=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:60]/[O:61][C:62]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:75]2[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=2)[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)/[C:27]([NH:29][C@@H:30]2[C:58](=[O:59])[N:32]3[C:33]([C:42]([O:44][CH:45]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[O:43])=[C:34]([S:81][C:82]4[CH:87]=[CH:86][N:85]=[CH:84][CH:83]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 88178710HCID 88178710, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 88179846HCID 88179846, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate (10.01 g, 8.98 m mol) in DMF (200 ml) was added 4-mercaptopyridine (2.00 g, 18.0 m mol) at −15° C., followed by dropwise addition of N,N-diisopropylethylamine (1.16 g, 8.98 m mol). The mixture was stirred at −15° C. for 4.5 hours and at 5° C. for 1 hour. The mixture was poured into a mixture of ice water (1.2 l) and 6N HCl (3 ml) and the precipitates were collected by filtration and washed with water. The powder was dissolved in THF, and ethyl acetate and water were added. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-(4-pyridylthio)-3-cephem-4-carboxylate (1.37 g).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with water
  3. dissolutionThe powder was dissolved in THF
  4. additionethyl acetate and water were added
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-13328e23d91e4880aa8eb3685724b640
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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