Chlorotrimethylsilane → HCID 86738910, compound

HRID 2166504Notes

Reaction equation

HRID 2166504 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[C@@H:15]([OH:17])[CH3:16])[C:9]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2].Cl[Si:33]([CH3:36])([CH3:35])[CH3:34]>N1C=CC=CC=1>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:18])[C@@H:12]2[C@@H:15]([O:17][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:16])[C:9]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 53962946HCID 53962946, compound

Product 1

HCID 86738910HCID 86738910, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Nitrobenzyl (5R,6S)-3-(2-acetamidoethylthio)-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (250 mg) in pyridine (7 ml) were treated with 70 mg. aliquots of chlorotrimethylsilane until all the starting hydroxycompound has reacted (4 aliquots required). The pyridine was removed by evaporation in vacuo, ethyl acetate (20 ml) was added to the residue and the resultant solution washed with water (20 ml). The ethyl acetate was dried (MgSO4) and evaporated in vacuo. Toluene (20 ml) was added to the residue and evaporated in vacuo to remove residual traces of pyridine. The crude silyl ether was then chromatographed on silica gel (0.040-0.063 mm; 15 g) eluting with ethyl acetate. Fractions containing the trimethylsilyl ether were combined and evaporated in vacuo to yield p-nitrobenzyl (5R, 6S)-3-(2-acetamidoethylthio)-6-[(1S)-1-trimethylsilyloxyethyl]7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (145 mg). Found M+ m/e 521.1657 C23H31N3O7SSi requires m/e 521.1650.

Workup

  1. customThe pyridine was removed by evaporation in vacuo, ethyl acetate (20 ml)
  2. additionwas added to the residue
  3. washthe resultant solution washed with water (20 ml)
  4. dry with materialThe ethyl acetate was dried (MgSO4)
  5. customevaporated in vacuo
  6. additionToluene (20 ml) was added to the residue
  7. customevaporated in vacuo
  8. customto remove residual traces of pyridine
  9. customThe crude silyl ether was then chromatographed on silica gel (0.040-0.063 mm; 15 g)
  10. washeluting with ethyl acetate
  11. additionFractions containing the trimethylsilyl ether
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-54eb402d31d84fc0ad8474630d435cbb
Source dataset
uspto-grants-1983_06
Patent number
US04387051

Reaction notes

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