Morpholine → HCID 178432458, compound

HRID 568249Notes

Reaction equation

HRID 568249 reaction equation
FC(F)(F)S([O-])(=O)=O.C(OC([N:15]1[C@H:19]([CH2:20][C:21]2[S:25][C:24]3=[CH:26][N:27]([CH2:30][CH:31]4[CH2:33][CH2:32]4)[C:28]([CH3:29])=[N+:23]3[CH:22]=2)[CH2:18][C@H:17]([S:34][C:35]2[C@H:36]([CH3:52])[C@@H:37]3[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:38]3[C:39]=2[C:40]([O:42]CC=C)=[O:41])[CH2:16]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>[CH2:32]1[CH2:33][CH:31]1[CH2:30][N:27]1[CH:26]=[C:24]2[S:25][C:21]([CH2:20][C@H:19]3[NH:15][CH2:16][C@@H:17]([S:34][C:35]4[C@H:36]([CH3:52])[C@@H:37]5[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:38]5[C:39]=4[C:40]([O-:42])=[O:41])[CH2:18]3)=[CH:22][N+:23]2=[C:28]1[CH3:29]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 178459452HCID 178459452, compound

Product 1

HCID 178432458HCID 178432458, compoundYield 6.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (0.7 ml) and 0.7 ml of dry ethanol are added to 47.9 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-cyclopropylmethyl)-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate. Triphenylphosphine (7.8 mg), 0.016 ml of morpholine, and 4.3 mg of tetrakis(triphenylphosphine)palladium(0) are successively added thereto, and the mixture is stirred in an argon atmosphere at room temperature for one hr. 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 2.0 mg of the title compound as a slightly yellow powder.

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-408ef77ccbe84f51b5d4d240424077c0
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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