Leucine, N-carboxy-, N-benzyl ester, L- → HCID 67626227, compound

HRID 1941303Notes

Reaction equation

HRID 1941303 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17](O)=O)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([NH2:31])[CH:25]=1.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.F[B-](F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]1[NH:31][C:26]2[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=[CH:28][C:27]=2[N:30]=1)[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 81531DiisopropylethylamineHCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 131720368HCID 131720368, compound

Product 1

HCID 67626227HCID 67626227, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of N-benzyloxycarbonyl-L-leucine (20 mmol, 5.3 g), 4-methoxy-1,2-phenylenediamine dihydrochloride (4.22 g, 20 mmol) and O-benzotriazole-N,N,N',N'-tetramethyl-uronium-tetrafluoroborate (TBTU) (6.58 g, 20.50 mmol) in 15 mL DMF cooled in an ice bath was added diisopropylethylamine (14 mL, 80 mmol). After stirring for 2 hours, ethyl acetate was added and the solution was washed with saturated NaHCO3 3 times and brine 3 times, dried (MgSO4), and concentrated. The crude product was dissolved in 30 mL acetic acid and the solution was heated at 65° C. for 2 hours. Acetic acid was removed by concentration under reduced pressure and the residue was purified on a silica gel column using methanol (3%)-methylene chloride as eluent to give 5.5 g (80%) product. m.p. 73°-77° C. ES-MS: calcd M+1 368.2; found 368.3.

Workup

  1. temperaturecooled in an ice bath
  2. washthe solution was washed with saturated NaHCO3 3 times and brine 3 times
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in 30 mL acetic acid
  6. customAcetic acid was removed by concentration under reduced pressure
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-26c395cecb3247b182e17dd0311371df
Source dataset
uspto-grants-1997_12
Patent number
US05703092

Reaction notes

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