Acetic Acid → HCID 11037511, compound

HRID 1374393Notes

Reaction equation

HRID 1374393 reaction equation
C(OC([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[N:14]=[C:15]([S:18][C:19]3[C@H:25]([CH3:26])[C@H:24]4[N:21]([C:22](=[O:30])[C@@H:23]4[C@H:27]([OH:29])[CH3:28])[C:20]=3[C:31]([O:33]CC=C)=[O:32])[S:16][CH:17]=2)[CH2:9][C@H:8]1[CH2:37][OH:38])=O)C=C.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC.P([O-])([O-])([O-])=O>ClCCl>[OH:29][C@@H:27]([C@H:23]1[C:22](=[O:30])[N:21]2[C@@H:24]1[C@@H:25]([CH3:26])[C:19]([S:18][C:15]1[S:16][CH:17]=[C:13]([C:10]3[CH2:9][C@@H:8]([CH2:37][OH:38])[NH:7][CH2:12][CH:11]=3)[N:14]=1)=[C:20]2[C:31]([OH:33])=[O:32])[CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1061PhosphateHCID 5948TributylstannaneHCID 86592509HCID 86592509, compound

Product 1

HCID 11037511HCID 11037511, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-({4-[(2S)-1-[(allyloxy)carbonyl]-2-(hydroxymethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-thiazol-2-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (28 mg, 0.05 mmol) in dichloromethane (4 ml) were added acetic acid (7.2 μl) and tributyltin hydride (135 ml, 0.50 mmol) and then was added at room temperature bis(triphenylphosphine)palladium chloride(II) (3.5 mg, 0.005 mmol). Ten minutes later the reaction mixture was poured into a mixture of ice (10 g) and phosphate buffer (pH7.0, 10 ml). After separation of the mixture with a separating funnel, the organic 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)-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-thiazol-2-yl}sulfanyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (3.9 mg) as a white amorphous.

Workup

  1. customAfter separation of the mixture with a separating funnel
  2. extractionthe organic 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-2293ae2aa90449dfb83deb5858055ea6
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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