Triethylamine → [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

HRID 1822154Notes

Reaction equation

HRID 1822154 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]([NH:31][C@@H:32]([C:36](O)=[O:37])[CH:33]([CH3:35])[CH3:34])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:27]([O:26][C:24](=[O:25])[NH:31][CH:32]([C:36](=[O:37])[NH:16][C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:33]([CH3:34])[CH3:35])([CH3:28])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10727275N-Benzyl-4-methyl-o-phenylenediamine

Product 1

HCID 66886932[1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N1-benzyl-4-methyl-benzene-1,2-diamine (1.24 mmol) and triethylamine (0.26 mL, 1.86 mmol) in dry DMF (5 mL), was added boc-D-valine (296 mg, 1.36 mmol) followed by TBTU (400 mg, 1.24 mmol). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was added. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered, and the filtrated was concentrated in vacuo. The crude material was purified by flash chromatography to yield [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester.

Workup

  1. washThe organic layer was washed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrated was concentrated in vacuo
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-93a18139c2b74c478fb1c4caa69e6942
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

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