Hydrochloric Acid → N-(2,6-dichlorobenzoyl)-4-(2-(N,N-dimethylamino)phenyl]-L-phenylalanine methyl ester

HRID 1060412Notes

Reaction equation

HRID 1060412 reaction equation
O[C:2](C(F)(F)F)=O.[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2N)=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].C=O.Cl.[BH3-][C:42]#[N:43].[Na+].C([O-])(O)=O.[Na+]>CCO>[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N:43]([CH3:42])[CH3:2])=[CH:26][CH:25]=1)[NH:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid3×HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 131723775N-(2,6-dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt

Product 1

HCID 53855608N-(2,6-dichlorobenzoyl)-4-(2-(N,N-dimethylamino)phenyl]-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt (90 mg) was dissolved in EtOH (5 mL). To this solution was added formalin (96 μL), 1 N HCl (234 μL) and NaCNBH3 (36 mg). The mixture was stirred for 0.5 h at room temperature, then a 1:1 mixture of EtOH (0.5 mL) and 1N HCl (0.5 mL) was added and the mixture was stirred overnight. Additional 1N HCl was added and the mixture was stirred for 0.5 h. The mixture was neutralized with NaHCO3 and extracted with EtOAc. The combined extracts were dried (MgSO4) and evaporated to give N-(2,6-dichlorobenzoyl)-4-[2-(N,N-dimethylamino)phenyl]-L-phenylalanine methyl ester.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. stirringthe mixture was stirred for 0.5 h
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d08274bf03c6419a92ef344a99039b10
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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