Triphenylphosphine → Allyl (1S,5R,6S)-1-methyl-2-(1,1-dioxo-2,5,6,7-tetrahydro-1-thia-2,6-diaza-cyclopenta[cd]phenalen-2-ylmethyl)-6-(1-(R)-allyloxycarbonyloxyethyl)-carbapen-2-em-3-carboxylate

HRID 1068564Notes

Reaction equation

HRID 1068564 reaction equation
CCOC(/N=N/C(OCC)=O)=O.O[CH2:14][C:15]1[C@H:16]([CH3:38])[C@@H:17]2[C@@H:27]([C@H:28]([O:30][C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH3:29])[C:26](=[O:37])[N:18]2[C:19]=1[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21].[S:39]1(=[O:55])(=[O:54])[C:43]2[CH:44]=[CH:45][C:46]3[CH2:47][NH:48][CH2:49][C:50]4[C:53]=3[C:42]=2[C:41](=[CH:52][CH:51]=4)[NH:40]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:38][C@@H:16]1[C@@H:17]2[C@@H:27]([C@H:28]([O:30][C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH3:29])[C:26](=[O:37])[N:18]2[C:19]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])=[C:15]1[CH2:14][N:40]1[C:41]2[C:42]3[C:53]4[C:50](=[CH:51][CH:52]=2)[CH2:49][NH:48][CH2:47][C:46]=4[CH:45]=[CH:44][C:43]=3[S:39]1(=[O:55])=[O:54]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 206661122,5,6,7-Tetrahydro-1-thia-2,6-diaza-cyclopenta[cd]phenalene 1,1-dioxide

Product 1

HCID 131722705Allyl (1S,5R,6S)-1-methyl-2-(1,1-dioxo-2,5,6,7-tetrahydro-1-thia-2,6-diaza-cyclopenta[cd]phenalen-2-ylmethyl)-6-(1-(R)-allyloxycarbonyloxyethyl)-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (2.25 mmol) is added to a cold (0° C.) solution of allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate (1.5 mmol), 2,5,6,7-tetrahydro-1-thia-2,6-diaza-cyclopenta[cd]phenalene-1,1-dioxide (1.5 mmol) and triphenylphosphine (2.25 mmol) in tetrahydrofuran (15 mL). The mixture is stirred at room temperature for 30 minutes then partitioned between ethyl acetate (100 mL) and water (100 mL). The water layer is extracted with ethyl acetate (50 mL) and the combined ethyl acetate layers are washed with saturated aqueous sodium chloride (50 mL), dried with magnesium sulfate, filtered, and evaporated. The crude product is purified by column chromatography to give the title compound.

Workup

  1. customthen partitioned between ethyl acetate (100 mL) and water (100 mL)
  2. extractionThe water layer is extracted with ethyl acetate (50 mL)
  3. washthe combined ethyl acetate layers are washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-672c6f05ad994ee8ad243315865d3d4d
Source dataset
uspto-grants-2001_06
Patent number
US06251890B1

Reaction notes

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