HCID 10255782, compound → HCID 131710752, compound

HRID 2398135Notes

Reaction equation

HRID 2398135 reaction equation
[Cl:1][CH:2]([Cl:16])[C:3]([O:5][N:6]=[C:7]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:8](Cl)=[O:9])=[O:4].[NH2:17][C@@H:18]1[C:49](=[O:50])[N:20]2[C:21]([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:22]([CH2:25][S:26][C:27]3[S:28][C:29]([CH3:32])=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12>C(OCC)(=O)C.C1OC1C>[Cl:1][CH:2]([Cl:16])[C:3]([O:5][N:6]=[C:7]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH:17][C@@H:18]1[C:49](=[O:50])[N:20]2[C:21]([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:22]([CH2:25][S:26][C:27]3[S:28][C:29]([CH3:32])=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12)=[O:9])=[O:4]

Participants

5

Reactant 2

HCID 10255782HCID 10255782, compoundHCID 54155233HCID 54155233, compound

Product 1

HCID 131710752HCID 131710752, compound

Reagents, catalysts & solvents 2

HCID 6378Propylene OxideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-dichloroacetoxyimino-2-(thien-2-yl)acetyl chloride (0.585 g.) in ethyl acetate (5 ml.) was added to a stirred suspension of diphenylmethyl 7β -amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate (1 g.) in ethyl acetate (10 ml.) and propylene oxide (1 ml.) at 20°. After 30 minutes all the solid had dissolved. The solution was washed with 2N-hydrochloric acid, saturated sodium bicarbonate solution, water and brine, dried and concentrated to give crude diphenylmethyl 7β-[2-dichloroacetoxyimino-2-(thien-2-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate (syn-isomer) as a solvated foam (1.567 g.) λmax. (EtOH)267.5 nm (e11 240), τ values (CDCl3) include 3.00 (singlet, -CHPh2), 3.75 (singlet; CHCl2) and 7.35 (singlet; CH3).

Workup

  1. dissolutionAfter 30 minutes all the solid had dissolved
  2. washThe solution was washed with 2N-hydrochloric acid, saturated sodium bicarbonate solution, water and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-47d0b2b9685e4dc4b2b9cffb5317bb97
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

Loading…