Triethylamine → HCID 178501499, compound

HRID 380173Notes

Reaction equation

HRID 380173 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C@H:5]([CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)[NH2:6].[CH2:14]([N:21]=[C:22]=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([NH:21][C:22]([NH2:6])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:2][O:3][C:4](=[O:13])[C@H:5]([CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)[NH2:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 178501497HCID 178501497, compound

Product 1

HCID 178501499HCID 178501499, compoundYield 72,618,880%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of histidine methyl ester hydrochloride (2.0 g, 4.3 mmol) in methylene chloride, at 0° C., was added benzyl isocyanate (0.58 mL, 0.63 g, 4.7 nmol) and triethylamine (1.32 mL, 9.5 mmol), and the solution was stirred overnight at room temperature. The solution was concentrated and the residue taken up in ethyl acetate. The solution was washed with water, saturated NaHCO3, brine, dried over MgSO4, and concentrated. The product was obtained as a white foam (1.09 g, 84%).

Workup

  1. concentrationThe solution was concentrated
  2. washThe solution was washed with water, saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d34a1dd4951c4470a20b8d26616b1482
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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