Sodium Carbonate → HCID 53468206, compound

HRID 2035402Notes

Reaction equation

HRID 2035402 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@@H:15]([O:16]COC)[C@H:14]([O:20]COC)[C@H:13]([O:24]COC)[CH:12]([CH2:28][O:29]COC)[O:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[CH2:33]([N:35]1[C:39](=[O:40])[CH2:38][N:37]([C:41]2[CH:46]=[CH:45][C:44](B3OC(C)(C)C(C)(C)O3)=[CH:43][CH:42]=2)[C:36]1=[O:56])[CH3:34].C(=O)([O-])[O-].[Na+].[Na+].Cl.CO>[Pd].CN(C)C=O.O>[Cl:9][C:8]1[CH:7]=[CH:6][C:5]([C@H:10]2[C@H:15]([OH:16])[C@@H:14]([OH:20])[C@H:13]([OH:24])[C@@H:12]([CH2:28][OH:29])[O:11]2)=[CH:4][C:3]=1[CH2:2][C:44]1[CH:43]=[CH:42][C:41]([N:37]2[CH2:38][C:39](=[O:40])[N:35]([CH2:33][CH3:34])[C:36]2=[O:56])=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 21893726Hydrochloride methanolHCID 58446362HCID 58446362, compoundHCID 67417308HCID 67417308, compound

Product 1

HCID 53468206HCID 53468206, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

A mixture of the product from step C (82 mg, 0.15 mmol), 3-ethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)imidazolidine-2,4-dione (which compound) (59 mg, 0.18 mmol, 1.2 equiv), sodium carbonate (48 mg, 0.45 mmol), and the palladium catalyst (0.12 mg, 0.015 mmol) in N,N-dimethylformamide/water (2:1, 2.1 mL) was heated at 80° C. under nitrogen for 4 h. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (4×). The combined extracts were dried over sodium sulfate, passed through a short pad of silica gel, and concentrated. The coupling product obtained was then stirred overnight with 6 N HCl/methanol (20:1 v/v) at room temperature. The reaction mixture was concentrated to dryness and the residual material was purified by flash column chromatography (eluent: dichloromethane/methanol 100:0 to 90:10) to provide 1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-3-ethylimidazolidine-2,4-dione (47 mg, 47%).

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (4×)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe coupling product obtained
  6. concentrationThe reaction mixture was concentrated to dryness
  7. customthe residual material was purified by flash column chromatography (eluent: dichloromethane/methanol 100:0 to 90:10)

Sources & evidence

ORD record
ord-c86039040fbf4dd191634325aa5cf106
Source dataset
uspto-grants-2013_11
Patent number
US08575114B2

Reaction notes

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