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

HRID 24645
Notes
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Reaction equation

HRID 24645 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-ed2acfd47fc34c418e9d5ccf348afa75
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes