Trifluoroacetate → HCID 131717055, compound

HRID 346392Notes

Reaction equation

HRID 346392 reaction equation
F[C:2](F)(F)[C:3]([O-:5])=[O:4].I[CH2:9][C:10]1[CH2:11][S:12][C@@H:13]2[C@H:33]([NH:34][C:35](=[O:66])[C:36](=[N:62][O:63][CH2:64][CH3:65])[C:37]3[N:38]=[C:39]([NH:42]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:40][CH:41]=3)[C:32](=[O:67])[N:14]2[C:15]=1[C:16]([O:18]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17].[SH:68][C:69]1[S:70][C:71]([C:74]2[CH:79]=[CH:78][C:77](O)=[C:76]([OH:81])[CH:75]=2)=[N:72][N:73]=1.C(=O)([O-])O.[Na+:86].[OH:87][CH2:88][C@@:89]1(OC[C@H](O)[C@@H](O)[C@@H]1O)O>O>[NH2:42][C:39]1[S:40][CH:41]=[C:37]([C:36](=[N:62][O:63][CH2:64][CH3:65])[C:35]([NH:34][C@@H:33]2[C:32](=[O:67])[N:14]3[C:15]([C:16]([O-:18])=[O:17])=[C:10]([CH2:9][S:68][C:69]4[S:70][C:71]([C:74]5[CH:79]=[CH:78][C:77]([O:5][C:3](=[O:4])[CH3:2])=[C:76]([O:81][C:88](=[O:87])[CH3:89])[CH:75]=5)=[N:72][N:73]=4)[CH2:11][S:12][C@H:13]23)=[O:66])[N:38]=1.[Na+:86]

Participants

7

Reactant 5

HCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 699210735831-80-2HCID 131717057HCID 131717057, compoundHCID 178515918HCID 178515918, compound

Product 1

HCID 131717055HCID 131717055, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The trifluoroacetate obtained by the same operation as in EXAMPLE 26 by using 800 mg (0.86 mmol) of benzhydryl 3-iodomethyl-7β-[2-ethoxyimino-2-(2-tritylaminothiazol-4-yl) acetamido]-3-cephem-4-carboxylate (syn-isomer) and 300 mg (1.33 mmol) of 2-mercapto-5-(3,4-dihydroxyphenyl)-1,3, 4-thiadiazole, was suspended in water and adjusted to pH6.5 with a saturated sodium hydrogencarbonate. The suspension was subjected to ODS column chromatography (LC Sorb RP-18, manufactured by Kemco Co.) and eluted with a 40% methanol aqueous solution. The fraction containing the desired compound was concentrated and freeze-dried to obtain 106 mg (yield: 16.6%) of the above identified compound.

Workup

  1. washeluted with a 40% methanol aqueous solution
  2. additionThe fraction containing the desired compound
  3. concentrationwas concentrated
  4. customfreeze-dried
  5. customto obtain 106 mg (yield: 16.6%) of the

Sources & evidence

ORD record
ord-7b3ef6f6229646bb98d104d832a21c49
Source dataset
uspto-grants-1991_10
Patent number
US05061794

Reaction notes

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