Water → HCID 131716116, compound

HRID 1607939Notes

Reaction equation

HRID 1607939 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]([C:40]1[N:41]=[C:42]([NH:45][C:46]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[S:43][CH:44]=1)[C:10]([NH:12][CH:13]1[C:38](=[O:39])[N:15]2[C:16]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:17]([CH2:20][Cl:21])[CH2:18][S:19][C@H:14]12)=[O:11].ClC1C=CC=C(C(OO)=[O:73])C=1.O>C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]([C:40]1[N:41]=[C:42]([NH:45][C:46]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[S:43][CH:44]=1)[C:10]([NH:12][CH:13]1[C:38](=[O:39])[N:15]2[C:16]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[C:17]([CH2:20][Cl:21])[CH2:18][S:19](=[O:73])[C@H:14]12)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 131716117HCID 131716117, compound

Product 1

HCID 131716116HCID 131716116, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (6.5 g) in ethyl acetate (40 ml) was added dropwise a solution of m-chloroperbenzoic acid (1.54 g) in ethyl acetate (10 ml) at 0° C. The mixture was stirred for two hours under ice-cooling and then poured into a mixture of ethyl acetate (50 ml) and water (100 ml). The organic layer was washed with brine and then dried. The solvent was evaporated in vacuo and the residue was pulverized with diisopropyl ether to give benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (6.90 g).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with brine
  3. customdried
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8908a481a3334a6a939f8effd697760f
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

Loading…