Sodium Thiosulfate → HCID 141551044, compound

HRID 1252311Notes

Reaction equation

HRID 1252311 reaction equation
[CH:1]([O:14][C:15]([CH2:17][O:18]/[N:19]=[C:20](/[C:51]1[N:52]=[C:53]([NH:56][C:57]([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[S:54][CH:55]=1)\[C:21]([NH:23][CH:24]1[C:49](=[O:50])[N:26]2[C:27]([C:33]([O:35][CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[C:28]([CH2:31][Cl:32])[CH2:29][S:30][C@H:25]12)=[O:22])=[O:16])([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.ClC1C=CC=C(C(OO)=[O:84])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH:1]([O:14][C:15]([CH2:17][O:18]/[N:19]=[C:20](/[C:51]1[N:52]=[C:53]([NH:56][C:57]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)([C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[S:54][CH:55]=1)\[C:21]([NH:23][CH:24]1[C:49](=[O:50])[N:26]2[C:27]([C:33]([O:35][CH:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[O:34])=[C:28]([CH2:31][Cl:32])[CH2:29][S:30](=[O:84])[C@H:25]12)=[O:22])=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 88643407HCID 88643407, compound

Product 1

HCID 141551044HCID 141551044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23.4 g (22.3 mmol) of benzhydryl 7-[(Z)-2-(benzhydryloxycarbonylmethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate was dissolved in 500 ml of methylene chloride, and 4.8 g (22.3 mmol) of m-chloroperbenzoic acid was added over a period of 10 minutes under cooling with ice. The mixture was stirred for further 20 minutes. After an addition of 150 ml of a 10% sodium thiosulfate aqueous solution, the reaction solution was subjected to liquid separation. The organic layer was washed with a 5% sodium bicarbonate aqueous solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a powder of the above identified compound (the powder was used to the subsequent reaction without purification).

Workup

  1. temperatureunder cooling with ice
  2. customthe reaction solution was subjected to liquid separation
  3. washThe organic layer was washed with a 5% sodium bicarbonate aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a powder of the
  7. customwas used to the subsequent reaction without purification)

Sources & evidence

ORD record
ord-bfe2fe3ce91348ffb8483b7c93a6582b
Source dataset
uspto-grants-1988_05
Patent number
US04742053

Reaction notes

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