Chlorotrimethylsilane → 3-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

HRID 1424315Notes

Reaction equation

HRID 1424315 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]([OH:15])[OH:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].CCN(C(C)C)C(C)C.C[Si](Cl)(C)C.[CH3:30][C:31]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[C:32]=1[C:33](Cl)=[O:34]>C(Cl)Cl>[B:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:2]([NH:1][C:33](=[O:34])[C:32]2[C:36]([CH3:41])=[CH:37][C:38]([CH3:40])=[CH:39][C:31]=2[CH3:30])[C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)([OH:15])[OH:14]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 53503p-BoronophenylalanineHCID 81531DiisopropylethylamineHCID 970382,4,6-Trimethylbenzoyl chloride

Product 1

HCID 576609483-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.5 g (7.18 mmol) of 2-amino-3-(4-boronophenyl)propionic acid were suspended in 50 ml DCM and 7.4 ml (43.1 mmol) DIPEA and refluxed for 20 min together with 4.5 ml (35 mmol) TMSCl. The solution was cooled in an ice bath and a solution of 1.44 g (7.9 mmol) 2,4,6-trimethylbenzoyl chloride in 5 ml DCM were added dropwise. The reaction mixture was stirred 2 h at room temperature, diluted with 100 ml DCM and washed with 2 N aqueous HCl. During this washing some product precipitated which was collected. The organic phase was extracted with 2 N NaOH twice. Upon acidifying of the combined basic phases the product precipitated, which was collected and dried together with the first precipitate. The crude product was used without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. washwashed with 2 N aqueous HCl
  3. customDuring this washing some product precipitated which
  4. customwas collected
  5. extractionThe organic phase was extracted with 2 N NaOH twice
  6. customprecipitated
  7. customwhich was collected
  8. customdried together with the first precipitate
  9. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-0c7bef94f99d4f2da8782cb9b47e5567
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

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