Triethylamine → HCID 86754810, compound

HRID 1603248Notes

Reaction equation

HRID 1603248 reaction equation
C(O[C:9]([NH:11][C@H:12]([C:20]([C@@H:22]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[N:24]([NH2:30])[C:23]1=[O:31])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])C1C=CC=CC=1.[H][H].C(N(CC)CC)C.[CH:41](/S(Cl)(=O)=O)=[CH:42]\[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>[Pd].C(OCC)(=O)C>[C:43]1(/[CH:42]=[CH:41]/[C:9]([NH:11][C@H:12]([C:20]([C@@H:22]2[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[N:24]([NH2:30])[C:23]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5369377(E)-2-phenylethene-1-sulfonyl chlorideHCID 70093171HCID 70093171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86754810HCID 86754810, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-15 °C

Procedure

(3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one (200 mg, 0.47 mmol) obtained in example 7, was hydrogenated with 300 mg of 10% palladium on activated carbon in 50 ml of ethyl acetate at 50 psi hydrogen pressure at room temperature for 2 hrs. After removal of catalyst by filtration, the desubstituted (3S,4S)-3-(L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one in ethyl acetate was cooled to -15 ° C. Then triethylamine (50 mg, 0.5 mmol) and trans-β-styrenesulfonyl chloride (95 mg, 0.47 mmol) were added at -15 ° C. Stirring was continued at a bath temperature of -10 to 5° C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) as eluent and the title compound (200 mg) was obtained as a white solid.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. customwas continued at a bath
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7b0c76e62404a0184447e9322ff3045
Source dataset
uspto-grants-1999_11
Patent number
US05986108

Reaction notes

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