Acetic Acid → Methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzylamino]benzoate

HRID 2417482Notes

Reaction equation

HRID 2417482 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH2:8][CH2:9][O:10][C:11]([CH2:13][NH:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][C:25]=2[NH2:26])[C:19]([O:21][CH3:22])=[O:20])=[O:12])=[O:7])=[CH:4][CH:3]=1.[N:29]1([C:34]([C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)=[O:35])[CH2:33][CH:32]=[CH:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH2:8][CH2:9][O:10][C:11]([CH2:13][NH:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][C:25]=2[NH:26][CH2:40][C:39]2[CH:38]=[CH:37][C:36]([C:34]([N:29]3[CH2:33][CH:32]=[CH:31][CH2:30]3)=[O:35])=[CH:43][CH:42]=2)[C:19]([O:21][CH3:22])=[O:20])=[O:12])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 69892547Methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-aminobenzoate

Product 1

HCID 69892488Methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzylamino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

660 mg (1.63 mmol) of methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-aminobenzoate and 431 mg (2.1 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde were dissolved in 10 ml of dichloromethane. 0.185 ml (3.26 mmol) of acetic acid was added to the solution, and they were stirred at room temperature for 30 minutes. 860 mg (4.1 mmol) of sodium triacetoxyborohydride was added to the obtained mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. stirringwere stirred at room temperature overnight
  2. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-d9f73791e0cc4a84aef838b511476abd
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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