Dicyclohexylcarbodiimide → benzhydryl (6R)-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1461171Notes

Reaction equation

HRID 1461171 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)/[C:27](O)=[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.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:76][CH:77]1[C:108](=[O:109])[N:79]2[C:80]([C:92]([O:94][CH:95]([C:102]3[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=3)[C:96]3[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=3)=[O:93])=[C:81](/[CH:84]=[CH:85]\[C:86]3[S:90][N:89]=[N:88][C:87]=3[CH3:91])[CH2:82][S:83][C@H:78]12>C1COCC1.C(Cl)Cl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)/[C:27]([NH:76][CH:77]2[C:108](=[O:109])[N:79]3[C:80]([C:92]([O:94][CH:95]([C:102]4[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=4)[C:96]4[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=4)=[O:93])=[C:81](/[CH:84]=[CH:85]\[C:86]4[S:90][N:89]=[N:88][C:87]=4[CH3:91])[CH2:82][S:83][C@H:78]23)=[O:28])[N:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 14621702benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate

Product 1

HCID 88523270benzhydryl (6R)-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 60.5%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (1.58 g, 2.35 mmol) was dissolved in a mixed solvent of THF-methylene chloride (20 ml-10 ml) and cooled to 5° C. HOBT (0.32 g, 2.4 mmol) was added to this reaction solution, then DCC (0.50 g, 2.4 mmol) was added and the mixture was stirred at the same temperature for 2 hours. The reaction solution was filtered, then benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (0.98 g, 2.0 mmol) was added to the filtrate and it was stirred at 5° C. for 22 hours. The reaction solution was concentrated and then the concentrate was purified by column chromatography thereby benzhydryl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (1.38 g, 60.5% yield) was obtained as a yellow powdered compound.

Workup

  1. filtrationThe reaction solution was filtered
  2. stirringwas stirred at 5° C. for 22 hours
  3. concentrationThe reaction solution was concentrated
  4. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-c40c30a8c19241c6af2314e0ca797d90
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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