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

HRID 1060417Notes

Reaction equation

HRID 1060417 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:29]=O)=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.[BH3-]C#N.[Na+]>CO.C1COCC1.O.[OH-].[K+]>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:21][CH:22]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 54369932N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester

Product 1

HCID 54323660N-(2,6-dichlorobenzoyl)-4-[2-[(phenylamino)methyl]phenyl]-L-phenylalanine methyl ester

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester (49.1 mg) was dissolved in a mixture of anhydrous MeOH (1 mL) and anhydrous THF (0.5 mL). Aniline (58.8 μL), HCl (53.8 μL of 4M in dioxane) and 3 Å molecular sieves were then added and the mixture was stirred under N2 at room temperature for 1 h. NaCNBH3 (4.06 mg) was added and the mixture was stirred for an additional 72 h. The pH of the mixture was brought to approximately 2 with 1N HCl to quench the reaction. The mixture was diluted with water and neutralized with 1M KOH. This was then extracted with CH2Cl2 and the combined organic extracts were dried (K2CO3) and evaporated. The residue was purified by preparative TLC (silica gel) using CH2Cl2 as eluent to give N-(2,6-dichlorobenzoyl)-4-[2-[(phenylamino)methyl]phenyl]-L-phenylalanine methyl ester (21.2 mg). ESMS: m/z 533 (MH+).

Workup

  1. stirringthe mixture was stirred for an additional 72 h
  2. customto quench
  3. customthe reaction
  4. extractionThis was then extracted with CH2Cl2
  5. dry with materialthe combined organic extracts were dried (K2CO3)
  6. customevaporated
  7. customThe residue was purified by preparative TLC (silica gel)

Sources & evidence

ORD record
ord-e20507215c62432398ac84c8c2fead42
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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