Toluene → 3-Acetoxy-7beta-phenylacetylaminocepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1729701Notes

Reaction equation

HRID 1729701 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C@@H: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]2[OH:36])=[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.C1(C)C=CC=CC=1.[C:44](OC(=O)C)(=[O:46])[CH3:45]>N1C=CC=CC=1>[C:1]1([CH:7]([O:14][C:15]([C@@H: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]2[O:36][C:44](=[O:46])[CH3:45])=[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

5

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 68141186benzhydryl (2R,6R,7R)-3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate

Product 1

HCID 681428623-Acetoxy-7beta-phenylacetylaminocepham-4alpha-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.312 g of 3 -hydroxy-7β-phenylacetylamino-cepham-4α-carboxylic acid diphenylmethyl ester in 15 ml of pyridine and 7 ml of acetic anhydride is left to stand for 16 hours at 0° C and after addition of 50 ml of toluene is evaporated under reduced pressure. The residue is taken up in ethyl acetate; the organic solution is washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. The residue is purified by means of preparative thin layer chromatography; a silica gel plate of 100 cm length is used and development is carried out with a 1:1 mixture of toluene and ethyl acetate. 3 -Acetoxy-7β-phenylacetylaminocepham-4α-carboxylic acid diphenylmethyl ester of Rf = 0.47 is obtained, melting at 162°-164° C after crystallisation from a mixture of methylene chloride and pentane; [α]D20 = + 55° ± 1° (c = 0.492 in chloroform); ultraviolet absorption spectrum (in 95% strength ethanol): λmax = 253 mμ (ε = 700), 258 mμ (ε = 820) and 265 mμ (ε = 660): infrared absorption spectrum (in methylene chloride): characteristic bands at 2.96μ, 5.66μ, 5.77μ, 5.97μ, 6.28μ and 6.71μ.

Workup

  1. waitis left
  2. customis evaporated under reduced pressure
  3. washthe organic solution is washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue is purified by means of preparative thin layer chromatography
  7. additiondevelopment is carried out with a 1:1 mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-3d43abbd8eae456f82dfcc3493a1276c
Source dataset
uspto-grants-1976_11
Patent number
US03989695

Reaction notes

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