m-Chloroperbenzoic acid → HCID 131713452, compound

HRID 1904123Notes

Reaction equation

HRID 1904123 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:15][CH2:16][C:17]1[CH2:18][S:19][C@@H:20]2[CH:40]([NH:41][C:42](=[O:77])[C:43]([C:52]3[N:53]=[C:54]([NH:57][C:58]([C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)[C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[S:55][CH:56]=3)=[N:44][O:45][CH:46]3[CH2:50][CH2:49][O:48][C:47]3=[O:51])[C:39](=[O:78])[N:21]2[C:22]=1[C:23]([O:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=[O:14])[CH3:13]>C(Cl)Cl>[O:9]=[S:19]1[C@@H:20]2[CH:40]([NH:41][C:42](=[O:77])[C:43]([C:52]3[N:53]=[C:54]([NH:57][C:58]([C:59]4[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=4)([C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)[C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)[S:55][CH:56]=3)=[N:44][O:45][CH:46]3[CH2:50][CH2:49][O:48][C:47]3=[O:51])[C:39](=[O:78])[N:21]2[C:22]([C:23]([O:25][CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[C:17]([CH2:16][O:15][C:12](=[O:14])[CH3:13])[CH2:18]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131713453HCID 131713453, compound

Product 1

HCID 131713452HCID 131713452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.420 g of m-chloro-perbenzoic acid in 8 ml of methylene chloride was added under an inert atmosphere to a stirred solution of 1.525 g of the product of Step A in 8 ml of methylene chloride cooled on an ice bath to 0° to 5° C. and the mixture was stirred for one hour at that temperature. The mixture was evaporated to dryness under reduced pressure and the residue was taken up in 20 ml of ethyl acetate. The organic phase was washed with aqueous sodium bicarbonate solution and then with aqueous sodium chloride until the wash waters were neutral, dried and evaporated to dryness under reduced pressure at a temperature less than 30° C. The residue was taken up in 10 ml of ether and the mixture was vacuum filtered at room temperature. The product was rinsed with ether to obtain 1.390 g of the syn isomer of diphenylmethyl 1-oxo-3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-oxo-3-tetrahydrofuranyloxyimino)-acetamido]-ceph-3-eme- 4-carboxylate in the form of a yellow product.

Workup

  1. temperaturecooled on an ice bath to 0° to 5° C.
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. washThe organic phase was washed with aqueous sodium bicarbonate solution
  4. customdried
  5. customevaporated to dryness under reduced pressure at a temperature less than 30° C
  6. filtrationfiltered at room temperature
  7. washThe product was rinsed with ether

Sources & evidence

ORD record
ord-10655082932e441fae8344eb678f17f0
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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