2-(Bromomethyl)tetrahydro-2H-pyran → HCID 131718599, compound

HRID 1729554Notes

Reaction equation

HRID 1729554 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23][CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[S:22])=[C:15](C(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][O:42]1>>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23][CH:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[S:22])=[C:15]([CH2:40][CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 131718600HCID 131718600, compound

Product 1

HCID 131718599HCID 131718599, compoundYield 71%

Procedure

Diphenylmethyl 7-phenylacetamido-3-acetylthio-3-cephem-4-carboxylate (1.68 g) was reacted with 2-bromomethyltetrahydropyran (1.92 ml) in accordance with the procedure of Example 1(b). The crude reaction product was purified by a column chromatography on a silica gel column (40 g) with elution using benzene-ethyl acetate (4:1 by volume) as eluent to collect fractions containing the titled compound. The fractions collected were concentrated and the oily residue was triturated with diisopropylether to give the titled compound (1.42 g; 71%) as powder.

Workup

  1. customThe crude reaction product
  2. customwas purified by a column chromatography on a silica gel column (40 g) with elution
  3. customto collect fractions
  4. additioncontaining the titled compound
  5. customThe fractions collected
  6. concentrationwere concentrated
  7. customthe oily residue was triturated with diisopropylether

Sources & evidence

ORD record
ord-7a1b481188d54552a8442c891a6639f7
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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