Potassium Carbonate → HCID 178473645, compound

HRID 638323Notes

Reaction equation

HRID 638323 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[S:23][CH:24]=3)[C:15](=[O:52])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2].C(=O)([O-])[O-].[K+].[K+].[CH2:59]([O:61][C:62]([O:64][CH:65](Br)[CH3:66])=[O:63])[CH3:60]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[S:23][CH:24]=3)[C:15](=[O:52])[N:10]2[C:11]=1[C:12]([O:14][CH:59]([O:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH3:60])=[O:13])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30215501-Bromoethyl ethyl carbonateHCID 13279147HCID 13279147, compound

Product 1

HCID 178473645HCID 178473645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(6R,7R)-3-Carbamoyloxymethyl-7-[(Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylic acid (1.1 g) was dissolved in N,N-dimethylformamide (5 ml) and stirred with potassium carbonate (105 mg) under nitrogen with ice-water cooling. After 10 minutes, 1-ethoxycarbonyloxy-1-ethyl bromide was added. After one hour, the mixtured was allowed to attain 21° and was stirred thus for three hours. The mixture was partitioned between ethyl acetate and aqueous hydrochloric acid. The aqueous layer was extracted with more ethyl acetate and the combined organic layers were washed twice with brine, dried with magnesium sulphate and concentrated. The residue was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 60%) in petroleum ether (bp 40° to 60°) to give the title compound (930 mg); [α]D21 +44.0° (c 1.30, CHCl3); λmax (ethanol) 230 nm (E1 cm1% 312), λ infl 236 nm (ED1% 295) and λnm (E1 cm1% 226).

Workup

  1. waitAfter one hour
  2. customto attain 21°
  3. customThe mixture was partitioned between ethyl acetate and aqueous hydrochloric acid
  4. extractionThe aqueous layer was extracted with more ethyl acetate
  5. washthe combined organic layers were washed twice with brine
  6. dry with materialdried with magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 60%) in petroleum ether (bp 40° to 60°)

Sources & evidence

ORD record
ord-338e246b3ff74475b96d254311a256fd
Source dataset
uspto-grants-1985_12
Patent number
US04560683

Reaction notes

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