Acetic Acid → HCID 22632538, compound

HRID 2417521Notes

Reaction equation

HRID 2417521 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][CH2:10][C:11]([O:13]CCC(=O)C1C=CC(Cl)=CC=1)=O.[C:31]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)#[N:32].[C:41]([OH:44])(=O)[CH3:42].[C:45](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:46].[Na+].[CH2:59](N(CC)CC)[CH3:60].Cl[CH2:67][Cl:68]>[OH-].[Na+].C(O)C.C(OCC)(=O)C>[Cl:68][C:67]1[CH:60]=[CH:59][C:42]([C:41]([N:9]2[CH2:8][C:7]3[CH:6]=[CH:5][C:4]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:3][C:2]=3[N:1]([CH2:37][C:36]3[CH:39]=[CH:40][C:33]([C:31]#[N:32])=[CH:34][CH:35]=3)[C:11](=[O:13])[CH2:10]2)=[O:44])=[CH:46][CH:45]=1

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 660424-CyanobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69892587HCID 69892587, compound

Product 1

HCID 22632538HCID 22632538, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.02 g (2.4 mmol) of methyl 3-[3-amino-4-(((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl)phenyl]propionate and 371 mg (2.8 mmol) of 4-cyanobenzaldehyde were dissolved in 100 ml of dichloromethane. 0.27 ml (4.8 mmol) of acetic acid was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 1300 mg (6.0 mmol) of sodium triacetoxyborohydride was added to the reaction 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 dissolved in a mixture of 10 ml of 1 N sodium hydroxide and 10 ml of ethanol, and the obtained solution was stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 10 ml of dichloromethane. 470 mg (2.8 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.5 ml (3.6 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated to obtain the title compound.

Workup

  1. stirringwere stirred at room temperature overnight
  2. stirringthe obtained solution was stirred at room temperature for 4 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-25f6c1b975e743269a3d7739cb3b4010
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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