HCID 68825497, compound → HCID 57754340, compound

HRID 226211Notes

Reaction equation

HRID 226211 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:10]=[C:11]([C@@H:15]([NH:17][C:18](=[O:20])[CH3:19])[CH3:16])[CH:12]=[CH:13][CH:14]=2)[O:3]1>CO>[C:18]([NH:17][C@H:15]([C:11]1[CH:10]=[C:9]([B:4]([OH:5])[OH:3])[CH:14]=[CH:13][CH:12]=1)[CH3:16])(=[O:20])[CH3:19]

Participants

3

Reactant 1

HCID 68825497HCID 68825497, compound

Product 1

HCID 57754340HCID 57754340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A4a.1 (1.23 g, 5 mmol), bis-pinacolatodiborane (1.33 g, 5 mmol), potassium acetate (1.47 g, 15 mmol) and palladium acetate (224 mg, 1 mmol) were added to degassed DMF (anhydrous). The reaction mixture was heated at 80° C. overnight. The next day additional palladium acetate was added (610 mg, 2.5 mmol) was added and the reaction mixture heated overnight. The reaction mixture was cooled to room temperature and filtered through a pad of silica gel (washing with ethyl acetate). The filtrate was concentrated under reduced pressure with provided approximately 1.41 g of (S)—N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide (LCMS (M+H)+=290.31). The product was dissolved in methanol and purified by reverse phase column chromatography (during which time the boronate ester underwent hydrolysis) to yield 875 mg (˜70%) of the chiral boronic acid. (M+H)+=208.17

Workup

  1. custompurified by reverse phase column chromatography (during which time
  2. customthe boronate ester underwent hydrolysis)

Sources & evidence

ORD record
ord-7bf5cad0bc4846b6a0e7387a3d429665
Source dataset
uspto-grants-2009_07
Patent number
US07557211B2

Reaction notes

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