Ethanol → HCID 131710572, compound

HRID 1973663Notes

Reaction equation

HRID 1973663 reaction equation
Br[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]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:7]2[C:8]=1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:28]([O:30][C:31]([CH:33]=[P:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:29].CCO>C(OCC)(=O)C>[CH2:28]([O:30][C:31]([C:33](=[P:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]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:7]2[C:8]=1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:32])[CH3:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 131710573HCID 131710573, compound

Product 1

HCID 131710572HCID 131710572, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of t-butyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (5.0 g., ca. 10.56 mmole.) in ethyl acetate (90 ml.) was treated with a solution of ethoxycarbonylmethylenetriphenylphosphorane (9.18 g, 26.4 mmole) in ehtyl acetate (110 ml.) and the mixture stirred at 27° for 22 hours, in the dark. The mixture was cooled to ca 3° and stirred for 2 hours after which time precipitated material was collected by filtration and treated as described in Example 1c to give the ylid (3.85 g, 49%) as photosensitive white prisms (from ethyl acetate), m.p. (darkening at ca 155°) ca 178° (decomp.), [α]D27 + 61.5° (C 1.6, CHCl3), λmax. (EtOH) 266 nm. (ε 10,360) and 272 nm. (ε 10,000); the infrared and p.m.r. spectra resembled those of material described above in Example 1c.

Workup

  1. temperatureThe mixture was cooled to ca 3°
  2. stirringstirred for 2 hours after which time
  3. customprecipitated material
  4. filtrationwas collected by filtration
  5. additiontreated
  6. customto give the ylid (3.85 g, 49%) as photosensitive white prisms (from ethyl acetate), m.p. (darkening at ca 155°) ca 178° (decomp.), [α]D27 + 61.5° (C 1.6, CHCl3), λmax

Sources & evidence

ORD record
ord-be7867256ba144d2b2c4892755da26bf
Source dataset
uspto-grants-1976_12
Patent number
US03998821

Reaction notes

Loading…