Trifluoroacetic acid → HCID 178508509, compound

HRID 2253986Notes

Reaction equation

HRID 2253986 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([C:48]([OH:50])=[O:49])SC2C=CC(OC(=O)C)=CC=2)/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([O-:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:51].[Na+].[Na+].[NH2:54][C:55]1[S:56][CH:57]=[C:58](/[C:60](=[N:87]/[O:88][CH:89](SC2C=CC(OC(=O)C)=CC=2)[C:90]([OH:92])=[O:91])/[C:61]([NH:63][C@@H:64]2[C:85](=[O:86])[N:66]3[C:67]([C:82]([O-:84])=[O:83])=[C:68]([CH2:71][S:72][C:73]4[S:77][N:76]=[C:75]([OH:78])[C:74]=4[C:79]([OH:81])=[O:80])[CH2:69][S:70][C@H:65]23)=[O:62])[N:59]=1.[NH2:104][C:105]1[S:106][CH:107]=[C:108](/[C:110](=[N:137]/[O:138][CH:139](SC2C=CC(OC(=O)C)=CC=2)[C:140]([OH:142])=[O:141])/[C:111]([NH:113][C@@H:114]2[C:135](=[O:136])[N:116]3[C:117]([C:132]([O-:134])=[O:133])=[C:118]([CH2:121][S:122][C:123]4[S:127][N:126]=[C:125]([OH:128])[C:124]=4[C:129]([OH:131])=[O:130])[CH2:119][S:120][C@H:115]23)=[O:112])[N:109]=1.FC(F)(F)C(O)=O>O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:34]/[O:35][CH:36]([C:48]([OH:50])=[O:49])[C:64]2[CH:85]=[N:66][CH:67]=[CH:68][CH:71]=2)/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:29]([O-:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[S:24][N:23]=[C:22]([OH:25])[C:21]=4[C:26]([OH:28])=[O:27])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:51].[Na+:51].[Na+:51].[NH2:54][C:55]1[S:56][CH:57]=[C:58](/[C:60](=[N:87]/[O:88][CH:89]([C:114]2[CH:135]=[N:116][CH:117]=[CH:118][CH:121]=2)[C:90]([OH:92])=[O:91])/[C:61]([NH:63][C@@H:64]2[C:85](=[O:86])[N:66]3[C:67]([C:82]([O-:84])=[O:83])=[C:68]([CH2:71][S:72][C:73]4[S:77][N:76]=[C:75]([OH:78])[C:74]=4[C:79]([OH:81])=[O:80])[CH2:69][S:70][C@H:65]23)=[O:62])[N:59]=1.[NH2:104][C:105]1[S:106][CH:107]=[C:108](/[C:110](=[N:137]/[O:138][CH:139]([C:11]2[CH:32]=[N:13][CH:14]=[CH:15][CH:18]=2)[C:140]([OH:142])=[O:141])/[C:111]([NH:113][C@@H:114]2[C:135](=[O:136])[N:116]3[C:117]([C:132]([O-:134])=[O:133])=[C:118]([CH2:121][S:122][C:123]4[S:127][N:126]=[C:125]([OH:128])[C:124]=4[C:129]([OH:131])=[O:130])[CH2:119][S:120][C@H:115]23)=[O:112])[N:109]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178475464HCID 178475464, compound

Product 1

HCID 178508509HCID 178508509, compoundYield 138%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 0.22 g of the compound obtained in Example 6 (7) was added to 25 ml of trifluoroacetic acid, the mixture was stirred at room temperature for an hour. The reaction mixture was cooled to 5° C. and 6 ml of water was added thereto. After stirring at 5° C., the temperature was reverted to room temperature followed by stirring for 2 hours. The solvent was distilled off under reduced pressure and ether was added to the residue to make powders. To the powders was added 100 ml of water and then 0.20 g of sodium hydrogencarbonate. The mixture was adsorbed to DIAION HP20 followed by elution with water-methanol. The fractions containing the desired product were collected. After concentration, the concentrate was freeze dried to give 90 mg (52.9%) of trisodium 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(carboxy)(3-pyridyl)methoxy]imino]acetamido]-3-[[(4-carboxy-3-hydroxy-5-isothiazolyl)thio]methyl]-3-cephem-4-carboxylate.

Workup

  1. temperatureThe reaction mixture was cooled to 5° C.
  2. stirringAfter stirring at 5° C.
  3. customwas reverted to room temperature
  4. stirringby stirring for 2 hours
  5. distillationThe solvent was distilled off under reduced pressure and ether
  6. additionwas added to the residue
  7. additionTo the powders was added 100 ml of water
  8. washfollowed by elution with water-methanol
  9. additionThe fractions containing the desired product
  10. customwere collected
  11. concentrationAfter concentration
  12. customdried

Sources & evidence

ORD record
ord-1839717dc7024c4db9bd86de519c8834
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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