Diisopropylethylamine → HCID 123782682, compound

HRID 1772623Notes

Reaction equation

HRID 1772623 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].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:18][C:2]1([CH3:1])[C:3]([CH3:17])([CH3:16])[O:4][B:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:43]3[CH2:47][CH2:46][CH2:45][C@H:44]3[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:13])=[CH:14][CH:15]=2)[O:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 123782682HCID 123782682, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (2.00 g, 8.06 mmol) in DMF (20 mL) was added HATU (6.20 g, 16.3 mmol), (S)-tert-butyl pyrrolidine-2-carboxylate (2.00 g, 11.7 mmol) and DIPEA (4.20 g, 32.5 mmol). The reaction mixture was stirred at rt overnight, and was quenched with H2O (20 mL). The resulting solution was extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:20-1:10 v/v) to obtain compound 17a as a yellow solid (1.40 g, 37% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H32BNO5: 402.2 (M+H). Found 402.1.

Workup

  1. customwas quenched with H2O (20 mL)
  2. extractionThe resulting solution was extracted with DCM (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with EtOAc/petroleum ether (1:20-1:10 v/v)

Sources & evidence

ORD record
ord-13ed002c5ca34b36a2da3b9dd1a630fb
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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