Triethylamine → HCID 28165569, compound

HRID 1627107Notes

Reaction equation

HRID 1627107 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2[CH:27]=[CH:28][CH:29]=[N:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1.CCN(CC)CC>C(Cl)Cl>[CH3:14][CH:13]([CH3:15])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:12])[N:30]1[CH2:29][CH2:28][CH2:27][CH2:25]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic 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 28165569HCID 28165569, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (1.0 g, 4.60 mmol), HATU (2.1 g, 5.52 mmol) and pyrrolidine (0.812 mL, 9.21 mmol) in DCM (30 mL) was added Et3N (1.28 mL, 9.21 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound as a light yellow oil (1.18 g, 95%). 1H NMR (400 MHz, CDCl3) δ 0.95 (d, J=18.95 Hz, 3 H) 0.95 (d, J=5.31 Hz, 3 H) 1.30-1.53 (m, 9 H) 1.77-2.07 (m, 5 H) 3.33-3.59 (m, 3 H) 3.59-3.80 (m, 1 H) 4.25 (dd, J=9.35, 6.57 Hz, 1 H) 5.30 (d, J=9.09 Hz, 1 H).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by silica column chromatography (MeOH/DCM, 0-10%)

Sources & evidence

ORD record
ord-90257a75ccff40958c436dedbe9e4ec3
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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