Acetonitrile → HCID 86760630, compound

HRID 1393063Notes

Reaction equation

HRID 1393063 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl.Cl.[NH2:24][C:25]1[CH:34]=[CH:33][C:32]([N:35]([CH3:37])[CH3:36])=[CH:31][C:26]=1[C:27](OC)=[O:28].[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].C(#N)C>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:27](=[O:28])[C:26]3[C:25](=[CH:34][CH:33]=[C:32]([N:35]([CH3:36])[CH3:37])[CH:31]=3)[NH:24][C:38]2=[O:39])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl esterHCID 66646350Benzoic acid, 2-amino-5-(dimethylamino)-, methyl ester, hydrochloride (1:2)

Product 1

HCID 86760630HCID 86760630, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

3 g of N-(t-butoxycarbonyl)-4-amino-L-phenylalanine methylester, 2.73 g of methyl 2-amino-5-(dimethylamino)benzoate dihydrochloride, 1.65 g of CDI (carbonyldiimidazole) and 50 mL of acetonitrile were stirred at room temperature. Then, 2.8 mL of triethylamine was added thereto and stirred at 60° C. overnight. After removing the solvent, the obtained residue was extracted with ethyl acetate, washed with water and saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After removing the solvent, the obtained residue was purified with silica gel column chromatography to obtain 2 g of the title compound.

Workup

  1. customAfter removing the solvent
  2. extractionthe obtained residue was extracted with ethyl acetate
  3. washwashed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customAfter removing the solvent
  6. customthe obtained residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-cb2cf685d27a4c709e667477bd48a996
Source dataset
uspto-grants-2008_03
Patent number
US07345049B2

Reaction notes

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