2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 14856084, compound

HRID 1032852Notes

Reaction equation

HRID 1032852 reaction equation
[Cl:1][CH2:2][C:3](=[O:11])/[C:4](=[N:8]/[O:9][CH3:10])/[C:5]([OH:7])=O.[NH2:12][CH:13]1[C:43](=[O:44])[N:15]2[C:16]([C:27]([O:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[C:17]([CH2:20][S:21][C:22]3[S:26][N:25]=[N:24][CH:23]=3)[CH2:18][S:19][C@H:14]12.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)Cl>[Cl:1][CH2:2][C:3](=[O:11])/[C:4](=[N:8]/[O:9][CH3:10])/[C:5]([NH:12][C@@H:13]1[C:43](=[O:44])[N:15]2[C:16]([C:27]([O:29][CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:28])=[C:17]([CH2:20][S:21][C:22]3[S:26][N:25]=[N:24][CH:23]=3)[CH2:18][S:19][C@H:14]12)=[O:7]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 9898994HCID 9898994, compoundHCID 69648672HCID 69648672, compound

Product 1

HCID 14856084HCID 14856084, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-(Z)-methoxyimino-3-oxobutanoic acid (4.05 g, 22.6 mmol.), diphenylmethyl 7-amino-3-[(1,2,3-thiadiazol-5-yl)thiomethyl]ceph-3-em-4-carboxylate (11.2 g, 22.6 mmol.) and 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (5.58 g, 22.6 mmol.) in 200 ml of methylene chloride was stirred at room temperature for 3 hours. The solution was evaporated to dryness at reduced pressure and the residue was taken up in 150 ml of ethyl acetate which was extracted with 50 ml aliquots of 1N hydrochloric acid, water, saturated sodium bicarbonate, water and brine. The ethyl acetate was dried over magnesium sulfate, evaporated to dryness and the resulting product was purified by flash chromatography on silica gel 60 using ethyl acetate: hexane (1:2) as the eluent to afford 3.34 g of the desired compound:NMR (CDCl3) δ 3.52 (pair of d, 2H, J=18 Hz, endocyclic --CH2S--), 4.05 (pair of d, 2H, J=13 Hz, exocyclic --CH2S--), 4.15 (S, 3H, --OCH3)j, 4.59 (S, 2H, ClCH2 --), 5.04 (d, 1H, J=4.7 Hz, 6H of 7ACA), 5.88 (dd, 1H, J=4.7 and 8.6 Hz, 7H of 7ACA), 6.89 (S, 1H, --CH--), 7.33 (m, 10H, aromatic H), 8.37 (S, 1H, thiadiazole H).

Workup

  1. customThe solution was evaporated to dryness at reduced pressure
  2. extractionwas extracted with 50 ml aliquots of 1N hydrochloric acid, water, saturated sodium bicarbonate, water and brine
  3. dry with materialThe ethyl acetate was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customthe resulting product was purified by flash chromatography on silica gel 60 using ethyl acetate: hexane (1:2) as the eluent

Sources & evidence

ORD record
ord-fb8c4ccc06844715891d6fd2b9f6aa53
Source dataset
uspto-grants-1990_09
Patent number
US04959495

Reaction notes

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