Propanal → HCID 131711203, compound

HRID 2419873Notes

Reaction equation

HRID 2419873 reaction equation
C1(P(=C[C:21]2[CH2:22][S:23][C@@H:24]3[C@H:44]([NH:45][C:46](=[O:53])[CH2:47][C:48]4[S:49][CH:50]=[CH:51][CH:52]=4)[C:43](=[O:54])[N:25]3[C:26]=2[C:27]([O:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:55](=O)[CH2:56][CH3:57].[CH2:59](Cl)Cl>>[CH:57]([C:21]1[CH2:22][S:23][C@@H:24]2[C@H:44]([NH:45][C:46](=[O:53])[CH2:47][C:48]3[S:49][CH:50]=[CH:51][CH:52]=3)[C:43](=[O:54])[N:25]2[C:26]=1[C:27]([O:29][CH:30]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])=[CH:56][CH2:55][CH3:59]

Participants

4

Reactant 3

HCID 527PropanalHCID 6344DichloromethaneHCID 53998408HCID 53998408, compound

Product 1

HCID 131711203HCID 131711203, compoundYield 10%

Procedure

Diphenylmethyl 3-(triphenylphosphoranylidenemethyl)-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (1.528 g., 2 mmole) was dissolved in a mixture of freshly distilled propionaldehyde (25 ml., 350 mmole) and dry methylene chloride (25 ml.). The solution was stirred at 25° for 16 hours, the solvent and residual propionaldehyde removed by rotary evaporation, and the residue dissolved in the methylene chloride (200 ml.). The resulting solution was washed successively with N-hydrochloric acid (200 ml.), 2N-aqueous sodium bicarbonate (200 ml.), water (200 ml.), brine (100 ml.), dried and evaporated to a yellow foam. This material was purified by column chromatography on Kieselgel. Combination of similar fractions (as judged by TLC) gave the title compound as pale yellow crystals (110 mg., 10%), RF 0.70, m.p. 156-158° (decomp.), [α]D - 10° (THF), λmax. 289 nm. (ε 8,700), inflexion at 235 nm. (ε14,600), νmax. (CHBr3) (--NH), 1782 (β-lactam), 1720 and 1230 (ester), 1684 and 1510 (--CONH--) cm. -1 ; the p.m.r. spectrum indicated that the compound was mainly the cis-isomer (with ca. 15% trans), with signals at τ 3.98 (--CH=CH.CH2CH3, d, J =11 Hz.), 4.23 (C(7)H, dd, J 5 and 9 Hz.), 4.61 (=CH.CH2CH3, complex m), 5.04 (C(6)H, d, J 5 Hz.), 6.6 and 6.83 (C(2) --CH2, AB-q,JAB 18 Hz.), 8.22 (--CH2CH3, complex m), 9.18 (--CH2CH3, methyl t, J 8 Hz.), [Found: C, 66.25; H, 5.2; N, 5.1; S, 11.6; C30H28N2O4S2 (544.7) requires C, 66.15; H, 5.2; N, 5.1; S, 11.8%].

Workup

  1. customthe solvent and residual propionaldehyde removed by rotary evaporation
  2. dissolutionthe residue dissolved in the methylene chloride (200 ml.)
  3. washThe resulting solution was washed successively with N-hydrochloric acid (200 ml.), 2N-aqueous sodium bicarbonate (200 ml.), water (200 ml.), brine (100 ml.)
  4. customdried
  5. customevaporated to a yellow foam
  6. customThis material was purified by column chromatography on Kieselgel

Sources & evidence

ORD record
ord-054e1d6ab0b74a75974a9286764ecc21
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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