Triethylamine → Benzhydryl (6R,7R)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1905797Notes

Reaction equation

HRID 1905797 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][CH:18]2O)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.CS([O-])(=O)=O>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 1364457351762-51-7

Product 1

HCID 11237070Benzhydryl (6R,7R)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 81.53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (2) in dimethylformamide (9.5 parts, dried over Molecular Sieves) cooling at -50° C. under nitrogen are added triethylamine (4 equivalents) and then methanesulfonyl chloride (2 equivalents) over 3 minutes at -52° to -45° C. After 2.5 hours at -55° to -45° C., the produced methanesulfonate (3) solution is stirred for 50 minutes at -15° to -12° C. diluted with ethyl acetate, washed with water, 5% hydrochloric acid, and water, dried over sodium sulfate, and concentrated. The residue is crystallized from methanol to give 7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (6). (Yield: 81.53%). mp. 166° C. (decomposition).

Workup

  1. washwashed with water, 5% hydrochloric acid, and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-ee4dd035e257403cbf9c7ca390ca8132
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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