Potassium Carbonate → HCID 54445672, compound

HRID 1006099Notes

Reaction equation

HRID 1006099 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:13][C@H:14]([CH2:18][OH:19])[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[C:5]([CH3:20])[C:4]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].[CH2:28]1[O:38][C:37]2[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][C:30]=2[O:29]1.[I-].[Li+]>CN(C)C=O.C(Cl)Cl>[CH2:28]1[O:38][C:37]2[CH:36]=[CH:35][C:32]([CH2:33][O:16][C:15](=[O:17])[C@H:14]([NH:13][S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:21])[C:5]=3[CH3:20])(=[O:11])=[O:12])[CH2:18][OH:19])=[CH:31][C:30]=2[O:29]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 18337555HCID 18337555, compound

Product 1

HCID 54445672HCID 54445672, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-hydroxypropionic acid (27.9 g, 87.9 mmol) in dimethylformamide (280 mL) at 0° C., was added potassium carbonate (72.9 g, 527 mmol) and a solution of 3,4-methylenedioxybenzyl chloride ((60 g, 170.8 mmol, 50% (w/w)) in methylene chloride. After 2 h, lithium iodide (5.88 g, 44 mmol) was added and the reaction mixture was warmed to rt. over 2 h. After 6 h, the reaction mixture was partitioned between ethyl acetate (600 mL) and water (250 mL). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. The crude residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes) to afford 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-hydroxypropionic acid 3,4-methylenedioxybenzyl ester (38.4 g) which was taken directly into the next reaction without further purification.

Workup

  1. waitover 2 h
  2. waitAfter 6 h
  3. customthe reaction mixture was partitioned between ethyl acetate (600 mL) and water (250 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-c21db40ee2524035a5f014e2587bb037
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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