1-Propanol → HCID 131710128, compound

HRID 1604924Notes

Reaction equation

HRID 1604924 reaction equation
Cl[CH:2](Cl)[C:3]([O:5][CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])=O.[CH2:29](O)CC>>[CH2:3]([O:5][CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])[CH2:2][CH3:29]

Participants

3

Reactant 2

HCID 10311-PropanolHCID 131710126HCID 131710126, compound

Product 1

HCID 131710128HCID 131710128, compoundYield 11.7%

Procedure

3-Dichloroacetoxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (5 g., 12.9 mmoles) was refluxed in n-propanol (50 ml.) for 20 minutes. The solution was cooled and the precipitated brown solid was filtered off and discarded. The filtrate was treated with water (300 ml.) and the pH adjusted to 8.5 with aqueous sodium bicarbonate. The solution was extracted with ethyl acetate (2 × 20 ml.) and the extracts were discarded. The aqueous phase was acidified to pH 1.5 and extracted with ethyl acetate (3 × 20 ml.). After drying, the solution was removed and the residue dissolved in ethyl acetate (50 ml.), and ether (100 ml.) was added. The precipitated brown solid was filtered off and discarded, and the filtrate evaporated to dryness. The residue was twice recrystallised from aqueous ethanol to give the title compound as colourless needles (500 mg., 11.7%), m.p. 152°-154° (decomp) [α]D25 = 79.8° (c 1.0, tetrahydrofuran), λmax (pH6-phosphate buffer) 236 nm. (ε = 13,600), 260 nm. (ε = 8,700) (shoulder), νmax (Nujol) 3310 (--NH--), 1772 (β-lactam), 1724 (--COOH), 1665 and 1535 cm-1 (--CONH--). (Found: C, 51.3; H, 5.1; N, 6.9; S, 15.9. C17H20N2S2O5 requires: C, 51.5; H, 5.1; N, 7.1; S, 16.2%). N.M.R. (D2O-NaHCO3) 5.78, 6.60, 8.52, 9.13τ (--CH2OCH2CH2CH3), Rf 0.48 (System B); 0.54 (System C).

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe precipitated brown solid was filtered off
  3. additionThe filtrate was treated with water (300 ml.)
  4. extractionThe solution was extracted with ethyl acetate (2 × 20 ml.)
  5. extractionextracted with ethyl acetate (3 × 20 ml.)
  6. customAfter drying
  7. customthe solution was removed
  8. dissolutionthe residue dissolved in ethyl acetate (50 ml.)
  9. additionether (100 ml.) was added
  10. filtrationThe precipitated brown solid was filtered off
  11. customthe filtrate evaporated to dryness
  12. customThe residue was twice recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-28a53f06c52d4d27b8dc094cc5da7014
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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