Ethyl Acetate → HCID 131720382, compound

HRID 725933Notes

Reaction equation

HRID 725933 reaction equation
O(P(O[C:18]1[C@H:19]([CH3:42])[C@H:20]2[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]2[C:22]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[SH:43][C@H:44]1[CH2:48][C@@H:47]([CH2:49][S:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:46]([C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][C:64]([N+:67]([O-:69])=[O:68])=[CH:63][CH:62]=2)=[O:58])[CH2:45]1.C(OCC)(=O)C>C(#N)C>[OH:40][C@@H:38]([C@H:37]1[C:36](=[O:41])[N:21]2[C:22]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])=[C:18]([S:43][C@H:44]3[CH2:48][C@@H:47]([CH2:49][S:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:46]([C:57]([O:59][CH2:60][C:61]4[CH:62]=[CH:63][C:64]([N+:67]([O-:69])=[O:68])=[CH:65][CH:66]=4)=[O:58])[CH2:45]3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15200286HCID 15200286, compoundHCID 22881097HCID 22881097, compound

Product 1

HCID 131720382HCID 131720382, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (2.24 g, 3.78 mmol) in acetonitrile (70 ml), DIPA (0.9 ml, 5.16 mmol) was added under cooling with ice, and then a solution of (3S,5S)-3-mercapto-1-p-nitrobenzyloxycarbonyl-5-(phenylthiomethyl)pyrrolidine (1.39 g, 3.42 mmol) in acetonitrile (15 ml) was dropwise added thereto. The reaction solution was stirred at 5° C. overnight, and ethyl acetate (300 ml) was added to the reaction solution. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate), to give p-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(3S,5S)-1-p-nitrobenzyloxycarbonyl-5-(phenylthiomethyl)pyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate (1.55 g, yield: 60%).

Workup

  1. temperatureunder cooling with ice
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-6c11ca545b704241a4507529837b4326
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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