Acetic Acid → HCID 58781984, compound

HRID 1374400Notes

Reaction equation

HRID 1374400 reaction equation
C(OC([N:7]1[CH2:11][CH:10]=[C:9]([C:12]2[N:13]=[C:14]([S:17][C:18]3[C@H:24]([CH3:25])[C@H:23]4[N:20]([C:21](=[O:29])[C@@H:22]4[C@H:26]([OH:28])[CH3:27])[C:19]=3[C:30]([O:32]CC=C)=[O:31])[S:15][CH:16]=2)[C@H:8]1[CH2:36][OH:37])=O)C=C.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC.P([O-])([O-])([O-])=O>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:28][C@@H:26]([C@H:22]1[C:21](=[O:29])[N:20]2[C@@H:23]1[C@@H:24]([CH3:25])[C:18]([S:17][C:14]1[S:15][CH:16]=[C:12]([C:9]3[C@@H:8]([CH2:36][OH:37])[NH:7][CH2:11][CH:10]=3)[N:13]=1)=[C:19]2[C:30]([OH:32])=[O:31])[CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1061PhosphateHCID 5948TributylstannaneHCID 86592514HCID 86592514, compound

Product 1

HCID 58781984HCID 58781984, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of allyl (4R,5S,6S)-3-({4-[(2S)-1-[(allyloxy)carbonyl]-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl)-6-[(1R)-1-hydoxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (33 mg, 0.06 mmol) in dicloromethane (3 ml) were added at 0° C. acetic acid (8.6 μl, 0.15 mmol), tributyltin hydride (165 ml, 0.61 mmol) and bis(triphenylphosphine)palladium chloride (4.2 mg, 0.006 mmol), and the mixture was stirred at the same temperature for 3 minutes. To the reaction mixture were added phosphate buffer (50 mM, pH7, 25 ml) and dichloromethane (5 ml). After separation of the aqueous layer, the dichloromethane layer was extracted twice with water and the aqueous layer was washed twice with dichloromethane (3 ml). The organic solvent in the aqueous layer was evaporated under reduced pressure, and the residue was purified by polymer chromatography (CHP-20P). The fractions eluted with 1–3% aqueous THF solution were combined and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (12.3 mg, 48%) as a white amorphous.

Workup

  1. customAfter separation of the aqueous layer
  2. extractionthe dichloromethane layer was extracted twice with water
  3. washthe aqueous layer was washed twice with dichloromethane (3 ml)
  4. customThe organic solvent in the aqueous layer was evaporated under reduced pressure
  5. customthe residue was purified by polymer chromatography (CHP-20P)
  6. washThe fractions eluted with 1–3% aqueous THF solution

Sources & evidence

ORD record
ord-24b5c38ce56a463a887223d43162b9ce
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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