Potassium Carbonate → HCID 88258899, compound

HRID 1421813Notes

Reaction equation

HRID 1421813 reaction equation
[C:1]([O:4][CH:5](Br)[CH3:6])(=[O:3])[CH3:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O-:32])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O:32][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 23690298Cefovecin sodium

Product 1

HCID 88258899HCID 88258899, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of (RS)-1-acetoxyethylbromide (267 mg) in 1-methyl-2-pyrrolidinone (2 ml) was added dropwise, over 1 hour, to an ice cold mixture of sodium (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (190 mg) and potassium carbonate (110 mg) in 1-methyl-2-pyrrolidinone (1 ml). After 15 minutes the mixture was diluted with ethyl acetate, washed with water, brine, dried (MgSO4), concentrated and flash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane to give the title compound (172 mg); νmax (CHCl3) 3019, 2929, 1786, 1683, 1520, 13176 and 1135 cm-1 ; δH (CDCl3, 250 MHz) 1.45-1.75 (4H,m), 1.90-2.10 (2H,m), 2.09 and 2.10 (together 3H, 2s), 2.30-2.50 (1H,m), 3.36 and 3.65 (2H, ABq, J 18.8 Hz), 4.93-5.10 (2H,m), 5.90-6.05 (1H,m), 6.94 and 7.07 (together 1H,q,J 5.8 Hz), 7.10 and 7.15 (together 1H, 2s) and 7.60 and 7.67 (together 1H,2d, J 7.4 Hz); [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (562)].

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane

Sources & evidence

ORD record
ord-951c75de1b0f44be94d8d794f03f949d
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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