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Morpholine → HCID 178496768, compound

HRID 568253
Notes
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Reaction equation

HRID 568253 reaction equation
[I-].C(OC([N:8]1[C@H:12]([CH2:13][C:14]2[S:18][C:17]3=[CH:19][N:20]([CH2:23][O:24][CH3:25])[C:21]([CH3:22])=[N+:16]3[CH:15]=2)[CH2:11][C@H:10]([S:26][C:27]2[C@H:28]([CH3:44])[C@@H:29]3[C@@H:39]([C@H:40]([OH:42])[CH3:41])[C:38](=[O:43])[N:30]3[C:31]=2[C:32]([O:34]CC=C)=[O:33])[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>[OH:42][C@@H:40]([C@H:39]1[C:38](=[O:43])[N:30]2[C:31]([C:32]([O-:34])=[O:33])=[C:27]([S:26][C@H:10]3[CH2:11][C@@H:12]([CH2:13][C:14]4[S:18][C:17]5=[CH:19][N:20]([CH2:23][O:24][CH3:25])[C:21]([CH3:22])=[N+:16]5[CH:15]=4)[NH:8][CH2:9]3)[C@H:28]([CH3:44])[C@H:29]12)[CH3:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 178459456allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-methoxymethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide

Product 1

HCID 178496768HCID 178496768, compoundYield 6.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 702EthanolSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (0.5 ml) and 0.5 ml of dry ethanol are added to 47.9 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-methoxymethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide. Triphenylphosphine (5.8 mg), 0.012 ml of morpholine, and 3.2 mg of tetrakis(triphenylphosphine)palladium(0) are successively added in an argon atmosphere at room temperature for 75 min. THF (10 ml) is added thereto, and 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 2.2 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-9fb70c9db33c4f48bebaf6d157d694cc
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06180622B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes