Sodium Thiosulfate → HCID 141551044, compound

HRID 653559Notes

Reaction equation

HRID 653559 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:73])[CH:24]([NH:25][C:26](=[O:72])/[C:27](=[N:53]\[O:54][CH2:55][C:56]([O:58][CH:59]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[O:57])/[C:28]3[N:29]=[C:30]([NH:33][C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH2:74][Cl:75])=[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:59]([O:58][C:56]([CH2:55][O:54]/[N:53]=[C:27](/[C:28]1[N:29]=[C:30]([NH:33][C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[S:31][CH:32]=1)\[C:26]([NH:25][CH:24]1[C:23](=[O:73])[N:22]2[C:17]([C:15]([O:14][CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:16])=[C:18]([CH2:74][Cl:75])[CH2:19][S:20](=[O:84])[C@H:21]12)=[O:72])=[O:57])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=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 under cooling with ice in 10 minutes. The mixture was further stirred for 20 minutes. To the reaction solution, 150 ml of a 10 % sodium thiosulfate aqueous solution was added for extraction. The organic layer was washed with a 5% sodium hydrogen carbonate aqueous solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a powder of the above-identified compound. The compound thus obtained was employed for the next reaction without purification

Workup

  1. temperatureunder cooling with ice in 10 minutes
  2. washThe organic layer was washed with a 5% sodium hydrogen carbonate aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a powder of the above-identified compound
  6. customThe compound thus obtained
  7. customwas employed for the next reaction without purification

Sources & evidence

ORD record
ord-fcb9078c0a3b4e9b83ad76facf13d0e3
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

Loading…