Tetrahydrofuran → HCID 10327839, compound

HRID 863346Notes

Reaction equation

HRID 863346 reaction equation
O1CCCC1.[CH3:6][N:7]([CH3:29])[C:8]([C@@H:10]1[CH2:14][C@H:13]([SH:15])[CH2:12][N:11]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])=[O:9].C([N-]C1CCCCC1)(C)C.Br[Mg+].C(N(CC)C(C1C=CC=CC=1S([C:55]1[C@H:56]([CH3:83])[C@@H:57]2[C@@H:74]([C@H:75]([O:77][Si:78]([CH3:81])([CH3:80])[CH3:79])[CH3:76])[C:73](=[O:82])[N:58]2[C:59]=1[C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([N+:70]([O-:72])=[O:71])=[CH:66][CH:65]=1)=[O:61])=O)=O)C>C(OCC)(=O)C>[CH3:6][N:7]([CH3:29])[C:8]([C@H:10]1[N:11]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)=[O:17])[CH2:12][C@@H:13]([S:15][C:55]2[C@H:56]([CH3:83])[C@@H:57]3[C@@H:74]([C@H:75]([O:77][Si:78]([CH3:81])([CH3:80])[CH3:79])[CH3:76])[C:73](=[O:82])[N:58]3[C:59]=2[C:60]([O:62][CH2:63][C:64]2[CH:65]=[CH:66][C:67]([N+:70]([O-:72])=[O:71])=[CH:68][CH:69]=2)=[O:61])[CH2:14]1)=[O:9]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 57294913HCID 57294913, compoundHCID 178456742HCID 178456742, compound

Product 1

HCID 10327839HCID 10327839, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2 ml of a tetrahydrofuran solution containing 68 mg (0.19 mmol) of (2S,4S)-2-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine were cooled in an ice bath, and then 0.19 ml (0.19 mmol) of a 1M tetrahydrofuran solution of bromomagnesium N-isopropyl-N-cyclohexylamide were added dropwise over a period of 2 minutes. The mixture was stirred for a further 10 minutes at this temperature, and then 1 ml of a tetrahydrofuran solution containing 100 mg of 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 38) was added. The mixture was stirred for a further 15 minutes at this temperature, after which ice water was added. The reaction solution was then diluted with ethyl acetate, washed with an aqueous solution of ammonium chloride then with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 10 g of silica gel, eluted with ethyl acetate, to give 94 mg (yield 78%) of the title compound as a foam-like solid.

Workup

  1. temperaturewere cooled in an ice bath
  2. additionwas added
  3. stirringThe mixture was stirred for a further 15 minutes at this temperature
  4. washwashed with an aqueous solution of ammonium chloride
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 10 g of silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-0d620e75d3bd46e7a83c8a36e9fc1c08
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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