Acetaldehyde → HCID 131711217, compound

HRID 2420569Notes

Reaction equation

HRID 2420569 reaction equation
C(=O)C.[C:4](O)(=O)[C:5]1C=CC=C[CH:6]=1.C1(P(=C[C:33]2[CH2:34][S:35][C@@H:36]3[C@H:56]([NH:57][C:58](=[O:65])[CH2:59][C:60]4[S:61][CH:62]=[CH:63][CH:64]=4)[C:55](=[O:66])[N:37]3[C:38]=2[C:39]([O:41][CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH:4]([C:33]1[CH2:34][S:35][C@@H:36]2[C@H:56]([NH:57][C:58](=[O:65])[CH2:59][C:60]3[S:61][CH:62]=[CH:63][CH:64]=3)[C:55](=[O:66])[N:37]2[C:38]=1[C:39]([O:41][CH:42]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])=[CH:5][CH3:6]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 243Benzoic AcidHCID 53998408HCID 53998408, compound

Product 1

HCID 131711217HCID 131711217, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetaldehyde (20 ml., 354 mmole) and benzoic acid (73 mg., 0.6 mmole) in dry methylene chloride (50 ml.) as stirred at 23° and treated, over 30 minutes, with diphenylmethyl 3-(triphenylphosphoranylidenemethyl)-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (1.528 g., 2 mmoles). After stirring for a further 4 hours, the solvent was removed in vacuo, the residue was extracted with ethyl acetate (50 ml.) and the insoluble material was filtered off; the filtrate was washed with saturated sodium bicarbonate (50 ml.), water (50 ml.) and brine (50 ml.), and dried and evaporated to a foam (1.58 g.). This material was purified by chromatography on 0.05-0.2mm. Kieselgel with benzene: ethyl acetate = 10:1 as eluent. Combination of similar fractions (as judged by t.l.c.) gave pale-yellow crystals of the title compound (178 mg., 17%), Rf 0.58, m.p. 144° to 148° (decomp.), [α]D -25.9° (CHCl3), λmax. 286.5 nm. (ε 7,900), with an inflexion at 237 nm. (ε 13,200); the p.m.r. spectrum indicated that the compound was mainly the cis-isomer (with 5-10% trans) with signals at τ 3.96 (--CH=CHCH3, d, J 12 Hz.), 4.51 (=CHCH3, dd, J 12 and 7 Hz.) and 8.61 (CH=CHCH3, methyl dd, J 7 and 0.5 Hz.) [Found: C, 65.2; H, 5.0; N, 5.2; S, 11.9; C29H26N2O4S2 (530.7) requires C, 65.6; H, 4.9; N, 5.3; S, 12.1%].

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe residue was extracted with ethyl acetate (50 ml.)
  3. filtrationthe insoluble material was filtered off
  4. washthe filtrate was washed with saturated sodium bicarbonate (50 ml.), water (50 ml.) and brine (50 ml.)
  5. customdried
  6. customevaporated to a foam (1.58 g.)
  7. customThis material was purified by chromatography on 0.05-0.2mm

Sources & evidence

ORD record
ord-43c4617990834948b3b1ec2fd98072f9
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

Loading…