Acetone → HCID 9543435, compound

HRID 1833894Notes

Reaction equation

HRID 1833894 reaction equation
CC(C)=O.[CH3:5][C:6]1([CH3:28])[C@H:10]([C:11]([OH:13])=[O:12])[N:9]2[C:14](=[O:26])[C@@H:15]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:8]2[S@:7]1=[O:27].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1.CC(C)=O>C(Cl)Cl>[CH3:5][C:6]1([CH3:28])[C@H:10]([C:11]([OH:13])=[O:12])[N:9]2[C:14](=[O:26])[C@@H:15]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@H:8]2[S@:7]1=[O:27]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 86735366HCID 86735366, compound

Product 1

HCID 9543435HCID 9543435, compoundYield 114%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of α-hydroxybenzyl polystyrene - 2% divinylbenzene coplymer [(10.0g., 0.029 mole) prepared according to the method G. L. Southard et al; Tetrahedron 1971, 27, 2701] in methylene chloride (50 ml.) was stirred for 1 hour at room temperature (18°-21°) to swell the polymer. To the suspension cooled to 5° was added (1S, 3S, 5R,6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide acetone solvate (20.40 g., 0.05 mole), followed by Toluene-p-sulphonyl chloride (14.30g., 0.075 mole), pyridine (12.1 ml., 11.85g., 0.15 mole; dried over KOH) and acetone (25 ml.). The mixture was stirred for 4 hours at 5°- 10°, during which an intense green colouration developed. The reaction mixture was filtered and pulled as dry as possible. The product was washed with chloroform (3 × 100 ml., containing 2% v/v ethanol), methanol (2 × 100 ml.), water (4 × 100 ml.), methanol (2 × 10 ml.) and chloroform (2 × 100 ml., containing 2% v/v ethanol); and drid to constant weight in vacuo at room temperature (18°-21°) to give a pale yellow polymer ester of (1S, 3S, 5R, 6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide (19.97g.). The composition was confirmed by microanalytical data and the infra red spectrum was identical with the product obtained in example 6 above. From the gain in weight, the penicillin moiety corresponds to 1.43 m.mole/g. of polymer.

Workup

  1. customprepared
  2. temperatureTo the suspension cooled to 5°
  3. filtrationThe reaction mixture was filtered
  4. customas dry as possible
  5. washThe product was washed with chloroform (3 × 100 ml
  6. addition, containing 2% v/v ethanol), methanol (2 × 100 ml.), water (4 × 100 ml.), methanol (2 × 10 ml.) and chloroform (2 × 100 ml
  7. addition, containing 2% v/v ethanol)
  8. customdrid to constant weight in vacuo at room temperature
  9. custom(18°-21°)

Sources & evidence

ORD record
ord-d2a8a92ca5d34c3795044d898f5520aa
Source dataset
uspto-grants-1978_01
Patent number
US04067858

Reaction notes

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