Propylene Oxide → HCID 54282420, compound

HRID 1833896Notes

Reaction equation

HRID 1833896 reaction equation
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH2:9][Cl:10])[CH2:7][S:8][C@H:3]12.C1OC1C.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:10][CH2:9][C:6]1[CH2:7][S:8][C@@H:3]2[C@H:2]([NH:1][C:26](=[O:27])[CH2:25][C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)[C:14](=[O:15])[N:4]2[C:5]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 1623622-Thiopheneacetyl chlorideHCID 11791565HCID 11791565, compound

Product 1

HCID 54282420HCID 54282420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of the polymer ester of (6R, 7R)-7-amino-3-chloromethylceph-3-em-4-carboxylic acid. (5.00g, from example 31(a) was stirred in methylene chloride (100 ml) under nitrogen for 30 minutes at room temperature 18-21 degrees). The mixture was cooled to 0° and propylene oxide (1.74 g, 0.03 ml) was added, and stirring continued for 30 min. Thienylacetylchloride (3.0 ml. 3.89 g. 0.024 ml) was added dropwise over a period of 10 minutes maintaining the temperature 0°-5°. When the addition was completed, stirring was continued for 15 minutes at 0°-5° and then for a further 5 hours allowing the temperature to rise to room temperature. The reaction mixture was filtered and pulled as dry as possible. The product was washed in methylene chloride (3 × 40 ml), methanol (2 × 40 ml), water (4 × 40 ml) methanol (2 × 40 ml), and methylene chloride (3 × 40 ml) and dried to constant weight in vacuo at 30° to give the yellow-orange coloured polymer ester of (6R, 7R)-3-chloromethyl-7-(2-thienylacetamido) ceph-3-em-4-carboxylic acid (5.10 g). A sample of the product on suspending in methylene chloride, spraying with a 0.5% solution of ninhydrin in butan-1-ol, and warming gave an orange colouration indicating that the starting product had been consumed and the title product had been formed.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. temperaturemaintaining the temperature 0°-5°
  3. additionWhen the addition
  4. stirringstirring
  5. waitwas continued for 15 minutes at 0°-5°
  6. waitfor a further 5 hours allowing
  7. customto rise to room temperature
  8. filtrationThe reaction mixture was filtered
  9. customas dry as possible
  10. washThe product was washed in methylene chloride (3 × 40 ml)
  11. dry with materialmethanol (2 × 40 ml), water (4 × 40 ml) methanol (2 × 40 ml), and methylene chloride (3 × 40 ml) and dried to constant weight in vacuo at 30°

Sources & evidence

ORD record
ord-3e2e0d6f938b4457afccbe808f5459df
Source dataset
uspto-grants-1978_01
Patent number
US04067858

Reaction notes

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