Iodomethyl pivalate → HCID 141573520, compound

HRID 1729558Notes

Reaction equation

HRID 1729558 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[OH:31])/[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[S:26])=[C:15]([CH2:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:33]([O:39][CH2:40]I)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[OH:31])/[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O:27][CH2:40][O:39][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[S:26])=[C:15]([CH2:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 104401Iodomethyl pivalateHCID 141573532HCID 141573532, compound

Product 1

HCID 141573520HCID 141573520, compoundYield 62.5%

Procedure

Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(tetrahydropyran-2-yl)methylthio-3-cephem-4-carboxylate (65 mg) was reacted with iodomethyl pivalate (46 mg) in accordance with the procedure of Example 4. The crude reaction product was purified by a column chromatography on a silica gel column (12 g) with elution using chloroform-methanol (10:1 by volume) as eluent to collect fractions containing the titled compound. The fractions so collected were concentrated to a small volume, to which was added diisopropylether dropwise and slowly, resulting in the deposition of crystals. The crystals were taken up by filtration, followed by washing with diisopropylether and drying, affording the titled compound (48 mg; 62%).

Workup

  1. customThe crude reaction product
  2. customwas purified by a column chromatography on a silica gel column (12 g) with elution
  3. customto collect fractions
  4. additioncontaining the titled compound
  5. customThe fractions so collected
  6. concentrationwere concentrated to a small volume, to which
  7. additionwas added diisopropylether dropwise
  8. customslowly, resulting in the deposition of crystals
  9. filtrationThe crystals were taken up by filtration
  10. washby washing with diisopropylether
  11. customdrying

Sources & evidence

ORD record
ord-3985196fa45d429ca6125224d2f5eede
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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