Potassium Carbonate → 1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 376595Notes

Reaction equation

HRID 376595 reaction equation
I[CH:2]([O:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])[CH3:3].[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:38]/[O:39][CH3:40])/[C:18]([NH:20][C@@H:21]2[C:36](=[O:37])[N:23]3[C:24]([C:33]([O-:35])=[O:34])=[C:25]([C@@H:28]4[CH2:32][CH2:31][CH2:30][O:29]4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:11][C:12]1[S:13][CH:14]=[C:15](/[C:17](=[N:38]/[O:39][CH3:40])/[C:18]([NH:20][C@@H:21]2[C:36](=[O:37])[N:23]3[C:24]([C:33]([O:35][CH:2]([O:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])[CH3:3])=[O:34])=[C:25]([C@@H:28]4[CH2:32][CH2:31][CH2:30][O:29]4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110106451-Iodoethyl isopropyl carbonateHCID 23690298Cefovecin sodium

Product 1

HCID 1415822621-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 19.9%

Reagents, catalysts & solvents 2

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

Procedure

A solution of (RS)-1-iodo-1-(propan-2-yl)oxycarbonyloxyethane (516mg) in 1-methyl-2-pyrrolidinone (2ml) was added dropwise over 45 mins 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 (237mg) and finely powdered potassium carbonate (276mg) in 1-methyl-2-pyrrolidinone (5ml). The mixture was stirred for an additional 15 mins, diluted with ethyl acetate, washed with water, brine, dried (magnesium sulphate), concentrated and flash chromatographed on silica gel eluting with 50, 60, 70, 80% ethyl acetate in hexane to give the title compound as a foam (58mg); vmax (CHCl3) 2960, 1787, 1760, 1682, 1633, 1519 and 1377cm-1 ; δ(CDCl3, 250MHz) 1.20-2.50 (13H, m), 3.35-3.80 (2H, m), 3.80-4.20 (2H, m), 4.22 (3H, s), 4.83-5.10 (2H, m), 5.85-6.00 (1H, m), 6.85-7.08 (1H, m), 7.27 (1H, s) and 7.76 (1H, br, m). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (606)].

Workup

  1. washwashed with water, brine
  2. dry with materialdried (magnesium sulphate)
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50, 60, 70, 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-be0e1741156d4b7685ce58cabd7ead6a
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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