Diisopropylethylamine → (S)-tert-Butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)butanoate

HRID 718636

Reaction equation

HRID 718636 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][B:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[O:4][C:3]1([CH3:17])[CH3:16].[NH2:19][C@@H:20]([CH:28]([CH3:30])[CH3:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:29][CH:28]([CH3:30])[C@H:20]([NH:19][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([B:5]2[O:4][C:3]([CH3:17])([CH3:16])[C:2]([CH3:1])([CH3:18])[O:6]2)=[CH:15][CH:14]=1)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 114626tert-Butyl L-valinateHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 123812944(S)-tert-Butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)butanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (2.0 g, 8.1 mmol) and (S)-tert-butyl 2-amino-3-methylbutanoate (2.0 g, 9.5 mmol) in DMF (10 mL) were added HATU (6.1 g, 16 mmol) and DIEA (4.2 g, 33 mmol). The reaction mixture was stirred at rt overnight. The reaction was then quenched with water (100 mL). The resulting mixture was extracted with DCM (2×100 mL), and the organic layer was concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:50)) to obtain compound 43a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H34BNO5: 404.3 (M+H). Found 404.1.

Workup

  1. customThe reaction was then quenched with water (100 mL)
  2. extractionThe resulting mixture was extracted with DCM (2×100 mL)
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:50))

Sources & evidence

ORD record
ord-14d3c46333c44293a5b6c184d775eb9e
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Linked notes

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