Triethylamine → HCID 57288260, compound

HRID 1016467Notes

Reaction equation

HRID 1016467 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18][CH2:19][C:20]#[N:21].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:19]([CH2:20][NH:21][C:10]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12])#[N:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2684732-((Tert-butoxycarbonyl)amino)-4-methylpentanoic acidHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 57288260HCID 57288260, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution comprised of 2-tert-butoxycarbonylamino-4-methylvaleric acid (5 g, 30 mmol) in DMF (20 mL) was cooled in an ice bath and then aminoacetonitrile hydrochloride (3 g, 30 mmol), PyBOP® (11.25 g, 21 mmol) and triethylamine (6 mL, 60 mmol) were added sequentially to the solution. The mixture was stirred for 2 hours and then concentrated under vacuum. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (40 mL). The organic layer was separated, washed with water, 1M hydrochloric acid (20 mL), water and brine, dried (MgSO4) and concentrated under reduced pressure. Product was purified from the residue using a plug of silica with ethyl acetate as the eluant to provide tert-butyl 1-cyanomethylcarbamoyl-3-methylbutylcarbamate.

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (40 mL)
  4. customThe organic layer was separated
  5. washwashed with water, 1M hydrochloric acid (20 mL), water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customProduct was purified from the residue

Sources & evidence

ORD record
ord-de7a5c6bb9314e05847d6d4d2d499c48
Source dataset
uspto-grants-2002_11
Patent number
US06476026B1

Reaction notes

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