Sodium Thiosulfate → HCID 13180419, compound

HRID 653557Notes

Reaction equation

HRID 653557 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:68])([O:10]/[N:11]=[C:12](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[S:46][CH:47]=1)\[C:13]([NH:15][CH:16]1[C:41](=[O:42])[N:18]2[C:19]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:20]([CH2:23][Cl:24])[CH2:21][S:22][C@H:17]12)=[O:14])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:77])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]([CH3:68])([O:10]/[N:11]=[C:12](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[S:46][CH:47]=1)\[C:13]([NH:15][CH:16]1[C:41](=[O:42])[N:18]2[C:19]([C:25]([O:27][CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:26])=[C:20]([CH2:23][Cl:24])[CH2:21][S:22](=[O:77])[C@H:17]12)=[O:14])[CH3:9])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 13180416HCID 13180416, compound

Product 1

HCID 13180419HCID 13180419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (10.3 mmol) of benzhydryl 7-[(Z)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem- 4-carboxylate was dissolved in 200 ml of methylene chloride, and 1.78 g (10.3 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, 40 ml of a 10% sodium thiosulfate aqueous solution was added for extraction. Then, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a powder of the above-identified compound.

Workup

  1. temperatureunder cooling with ice in 10 minutes
  2. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain a powder of the above-identified compound

Sources & evidence

ORD record
ord-8f5b0d3a143648b782163abf184f9437
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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