Ethyl Acetate → HCID 54369112, compound

HRID 620801Notes

Reaction equation

HRID 620801 reaction equation
C(OC([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27]CC=C)=[O:26])[CH2:9][C@H:8]1[CH2:31][O:32][CH2:33][CH2:34][NH:35][C:36]([NH2:38])=[O:37])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=O)CC(=O)C1.C(OCC)(=O)C>O1CCCC1.O.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>[OH:23][C@@H:21]([C@H:17]1[C:16](=[O:24])[N:15]2[C@@H:18]1[C@@H:19]([CH3:20])[C:13]([S:12][C@@H:10]1[CH2:11][NH:7][C@H:8]([CH2:31][O:32][CH2:33][CH2:34][NH:35][C:36]([NH2:38])=[O:37])[CH2:9]1)=[C:14]2[C:25]([OH:27])=[O:26])[CH3:22]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 31358DimedoneHCID 54429917HCID 54429917, compound

Product 1

HCID 54369112HCID 54369112, compoundYield 54.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.73 g) in a mixture of tetrahydrofuran (34 ml) and water (11 ml) were added triphenylphosphine (0.41 g), dimedone (1.32 g) and tetrakis(triphenylphosphine)palladium(0) (0.18 g) successively with stirring at ambient temperature. The mixture was stirred at the same temperature for 3 hours. To the solution were added ethyl acetate (50 ml) and water (30 ml). The aqueous layer was separated and washed 3 times with ethyl acetate (30 ml). This aqueous layer was concentrated in vacuo to remove the organic solvent. The residue was chromatographed on activated charcoal (made by Wako Pure Chemical Industries) (30 ml) eluting in turn with water (90 ml) and 15% aqueous isopropyl alcohol (200 ml). The fractions containing the desired compound were collected and lyophilized to give (4R,5S, 6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-1azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.73 g).

Workup

  1. stirringThe mixture was stirred at the same temperature for 3 hours
  2. customThe aqueous layer was separated
  3. washwashed 3 times with ethyl acetate (30 ml)
  4. concentrationThis aqueous layer was concentrated in vacuo
  5. customto remove the organic solvent
  6. customThe residue was chromatographed on activated charcoal (made by Wako Pure Chemical Industries) (30 ml)
  7. washeluting in turn with water (90 ml) and 15% aqueous isopropyl alcohol (200 ml)
  8. additionThe fractions containing the desired compound
  9. customwere collected

Sources & evidence

ORD record
ord-d5a9c3ce13b74583af06cd764e7a2ddd
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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