Tetrahydrofuran → HCID 131722706, compound

HRID 1068571Notes

Reaction equation

HRID 1068571 reaction equation
[N:1]1([C:6]([S-:8])=[S:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([NH+](CC)CC)C.[Cl-].[Li+].O1CCCC1.O(P(O[C:40]1[C@H:41]([CH3:64])[C@H:42]2[C@@H:59]([C@H:60]([OH:62])[CH3:61])[C:58](=[O:63])[N:43]2[C:44]=1[C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[CH:51][CH:50]=1)=[O:46])(OC1C=CC=CC=1)=O)C1C=CC=CC=1>O.C(OCC)(=O)C>[OH:62][C@@H:60]([C@H:59]1[C:58](=[O:63])[N:43]2[C:44]([C:45]([O:47][CH2:48][C:49]3[CH:50]=[CH:51][C:52]([N+:55]([O-:57])=[O:56])=[CH:53][CH:54]=3)=[O:46])=[C:40]([S:7][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[S:8])[C@H:41]([CH3:64])[C@H:42]12)[CH3:61]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 15200286HCID 15200286, compoundHCID 88227470HCID 88227470, compound

Product 1

HCID 131722706HCID 131722706, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylammonium 1-pyrrolidinyldithiocarboxylate (1.0 g, 4.03 mmol) and lithium chloride (171 mg, 4.03 mmol) were added to a tetrahydrofuran solution (50 ml) of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (2.0 g, 3.36 mmol) at room temperature. The mixture was stirred at that temperature overnight in a nitrogen stream, and poured in a mixed liquid of ethyl acetate and water. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (Wakogel™ C-300, n-heptane-ethyl acetate 1:1→2:3) to give p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[(1-pyrrolidinyl)thiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (1.21 g, yield: 74%).

Workup

  1. washThe organic layer was washed with saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17eda213a2f745d88d04b67849ffd909
Source dataset
uspto-grants-2001_06
Patent number
US06251891B1

Reaction notes

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