Acetic Acid → p-Nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 622439Notes

Reaction equation

HRID 622439 reaction equation
C(O)(=[O:3])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:23]1([S:29][C:30]2[CH:31]([CH3:61])[C@@H:32]3[C@H:49]([C@H:50]([C:56](C)(C)C)CO[SiH](C)C)[C:48](=[O:60])[N:33]3[C:34]=2[C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.C(OCC)(=O)C>[C:23]1([S:29][C:30]2[CH:31]([CH3:61])[C@@H:32]3[C@@H:49]([C@H:50]([OH:3])[CH3:56])[C:48](=[O:60])[N:33]3[C:34]=2[C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131715712p-nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-t-butyldimethylsilyl-oxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 22839821p-Nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

300 μl of acetic acid and 2.1 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran were added to a solution of 298 mg of p-nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-t-butyldimethylsilyl-oxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate in 6.4 ml of tetrahydrofuran, kept at 0° to 5° C. with ice-water cooling. The mixture was kept stirred overnight at room temperature, and then for 4 hours in an oil bath at 30° C. The reaction mixture was then diluted with ethyl acetate and washed successively with saturated aqueous sodium chloride solution, 5% aqueous sodium bicarbonate solution, and again saturated aqueous sodium chloride solution. The solvent was distilled off, and the resulting residue was chromatographed on a column of silica gel using a 3/1 mixture of benzene/ethyl acetate as eluent, giving 57 mg of the title compound as pale yellow crystals.

Workup

  1. waitfor 4 hours in an oil bath at 30° C
  2. washwashed successively with saturated aqueous sodium chloride solution, 5% aqueous sodium bicarbonate solution, and again saturated aqueous sodium chloride solution
  3. distillationThe solvent was distilled off
  4. customthe resulting residue was chromatographed on a column of silica gel using
  5. additiona 3/1 mixture of benzene/ethyl acetate as eluent

Sources & evidence

ORD record
ord-b141b8e45021478ca97986d73d4d8520
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

Loading…