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Acetic Acid → 5-Chloro-2-(4-fluorobenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

HRID 275869
Notes
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Reaction equation

HRID 275869 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=1.[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.C(O)(=O)C.[BH4-].C([Na])#N>CO>[Cl:25][C:22]1[CH:23]=[CH:24][C:2]([NH:1][CH2:31][C:30]2[CH:33]=[CH:34][C:27]([F:26])=[CH:28][CH:29]=2)=[C:3]([CH:21]=1)[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 543159585-Chloro-2-(4-fluorobenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol produced in Example (1) (0.5 g) and 4-fluorobenzaldehyde (0.2 g). To the solution were added acetic acid (0.1 g) and cyano sodium borohydride (0.1 g). The mixture was concentrated, to which were added water (60 ml) and ethyl acetate (50 ml), followed by extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off to leave 5-chloro-2-(4-fluorobenzylamino)-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.56 g) as a colorless oily product.

Workup

  1. concentrationThe mixture was concentrated, to which
  2. additionwere added water (60 ml) and ethyl acetate (50 ml)
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-5fb7a81868264ae3ac4a717b596f8fb2
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352982B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes