Ethyl Acetate → Acetoxymethyl (6R,7R)-7-phenylacetamido-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

HRID 1421807Notes

Reaction equation

HRID 1421807 reaction equation
NC1S[CH:4]=[C:5](/[C:7](=N/OC)/[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:23]([O:25]COC(=O)C(C)(C)C)=O)=[C:15]([C@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])N=1.[C:39](=[O:42])([O-:41])[O-].[K+].[K+].[C:45]([O:48]CBr)(=O)[CH3:46].C(OCC)(=O)C.CN1[CH2:62][CH2:61][CH2:60][C:59]1=O>O>[C:5]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:23]([O:41][CH2:39][O:42][C:45](=[O:48])[CH3:46])=[O:25])=[C:15]([CH:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:62]=[CH:61][CH:60]=[CH:59][CH:4]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 68536Bromomethyl acetateHCID 882588472,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2R)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 53945347Acetoxymethyl (6R,7R)-7-phenylacetamido-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (6R,7R)-7-phenylacetamido-3-(tetrahydro-furan-2-yl)ceph-3-em-4-carboxylic acid (0.303 g, 0.78 mmol) (obtained in Example 12) in N-methylpyrrolidinone (5 ml) was added potassium carbonate (0.37 g, 2.66 mmol). Bromomethyl acetate (0.30 g, 1.95 mmol) was added dropwise to the mixture over 1 h. The mixture was stirred for a further 1 h, then ethyl acetate and water were added. The organic phase was washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by chromatography to give the title compound as a mixture of diastereomers (0.198 g, 56%); major diastereomer(S); δH (CDCl3) 1.59 (1H, m), 1.95 (2H, m), 2.12 (3H, s), 2.38 (1H, m), 3.28 (1H, d, J 18.9 Hz), 3.59 (1H, d), 3.65 (2H, ABq, J 16.4 Hz), 3.88 (2H, m), 4.89 (1H, dd, J 9.0, 6.7 Hz), 4.93 (1H, d, J 4.9 Hz), 5.84 (3H, m), 6.01 (1H, d, 9.1 Hz) and 7.34 (5H, m)

Workup

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-dc55f1ab7e1341ff9b8de61d7abb1469
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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