Morpholine → HCID 178472594, compound

HRID 568255Notes

Reaction equation

HRID 568255 reaction equation
[Br-].C(OC([N:8]1[C@H:12]([CH2:13][C:14]2[S:18][C:17]3=[CH:19][N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:21]([CH3:22])=[N+:16]3[CH:15]=2)[CH2:11][C@H:10]([S:29][C:30]2[C@H:31]([CH3:47])[C@@H:32]3[C@@H:42]([C@H:43]([OH:45])[CH3:44])[C:41](=[O:46])[N:33]3[C:34]=2[C:35]([O:37]CC=C)=[O:36])[CH2:9]1)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C(O)C>[CH2:27]([O:26][C:24]([CH2:23][N:20]1[CH:19]=[C:17]2[S:18][C:14]([CH2:13][C@H:12]3[NH:8][CH2:9][C@@H:10]([S:29][C:30]4[C@H:31]([CH3:47])[C@@H:32]5[C@@H:42]([C@H:43]([OH:45])[CH3:44])[C:41](=[O:46])[N:33]5[C:34]=4[C:35]([O-:37])=[O:36])[CH2:11]3)=[CH:15][N+:16]2=[C:21]1[CH3:22])=[O:25])[CH3:28]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 178459454HCID 178459454, compound

Product 1

HCID 178472594HCID 178472594, compoundYield 4.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (0.6 ml) and 0.6 ml of dry ethanol are added to 49.7 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-ethoxycarbonylmethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate bromide. Triphenylphosphine (6.9 mg), 0.014 ml of morpholine, and 3.8 mg of tetrakis(triphenylphosphine)palladium(0) are successively added thereto, and the mixture is stirred in an argon atmosphere at room temperature for 55 min. THF (10 ml) is added, the resultant precipitate is further washed twice with 3 ml of THF and dried in vacuo to give a yellow powder which is then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol) to give 1.6 mg of the title compound as a colorless flocculent material.

Workup

  1. washthe resultant precipitate is further washed twice with 3 ml of THF
  2. customdried in vacuo
  3. customto give a yellow powder which
  4. customis then purified by column chromatography on Cosmosil 40C18-PREP (water-methanol)

Sources & evidence

ORD record
ord-f2424066ec514616ae71babdb436e75f
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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