Triethylamine → HCID 28165828, compound

HRID 1968206Notes

Reaction equation

HRID 1968206 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2[CH:28]=[CH:29][CH:30]=[N:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1.CCN(CC)CC>C(Cl)Cl>[CH3:15][CH:14]([CH3:16])[CH2:13][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:12])[N:31]1[CH2:30][CH2:29][CH2:28][CH2:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 637604tert-Butoxycarbonyl-D-leucineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 28165828HCID 28165828, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-2-(tert-butoxycarbonylamino)-4-methylpentanoic acid (1.0 g, 4.32 mmol), HATU (1.97 g, 5.19 mmol) and pyrrolidine (0.76 mL, 8.65 mmol) in DCM (30 mL) was added Et3N (1.2 mL, 8.65 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 (1.17g, 95%).

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-a18d258e0d364d0da32394fe35c24573
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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