Pyridine → Methyl (2R,3S)-3-(9-anthracenesulfonamido)-3-phenyl-2-hydroxypropionate

HRID 1106992Notes

Reaction equation

HRID 1106992 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].N1C=CC=CC=1.[CH:21]1[C:34]2[C:25](=[CH:26][C:27]3[C:32]([C:33]=2[S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH:31]1[C:32]2[C:27](=[CH:26][C:25]3[C:34]([C:33]=2[S:35]([NH:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@@H:4]([OH:13])[C:3]([O:2][CH3:1])=[O:14])(=[O:37])=[O:36])=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15310604Anthracene-9-sulfonyl chlorideHCID 21968353(3S)-3-Phenylisoserine methyl ester

Product 1

HCID 57078772Methyl (2R,3S)-3-(9-anthracenesulfonamido)-3-phenyl-2-hydroxypropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3S)-3-Phenylisoserine methyl ester (I, 0.38 g, 1.95 mmol) is dissolved in methylene chloride (5 mL) and pyridine (1 mL) and the solution treated with a suspension of 9-anthracenesulfonylchloride (0.536 g, 1.95 mmol). The reaction is stirred at 23° for 90 min. The reaction is then poured into methylene chloride and extracted with hydrochloric acid (1 N) and aqueous bicarbonate (5%) and dried over magnesium sulfate. Concentration of the organic layer under reduced pressure produces crude product. This concentrate is chromatographed (silica gel 60; ethyl acetate/toluene, 20/80) to give the title compound, TLC (silica gel GF) Rf =0.38 in (ethyl acetate/toluene, 2/8); NMR (CDCl3, TMS) 3.11, 3.57, 4.18, 4.78, 6.22, 6.59, 6.67, 7.50, 7.55-7.75, 7.92, 8.09, 8.47 and 9.15 δ

Workup

  1. extractionextracted with hydrochloric acid (1 N) and aqueous bicarbonate (5%)
  2. dry with materialdried over magnesium sulfate
  3. customConcentration of the organic layer under reduced pressure produces crude product
  4. customThis concentrate is chromatographed (silica gel 60; ethyl acetate/toluene, 20/80)

Sources & evidence

ORD record
ord-6566d95d5c444924bcf3b259588df077
Source dataset
uspto-grants-2000_05
Patent number
US06057452

Reaction notes

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