Dimethylamine, hydrochloride → HCID 53913110, compound

HRID 1872168Notes

Reaction equation

HRID 1872168 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C:5]([NH:12][C@H:13]([C:22]([OH:24])=O)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]>ClCCl.CN(C=O)C>[C:8]([O:7][C:5](=[O:6])[NH:12][C@H:13]([C:22](=[O:24])[N:3]([CH3:4])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 53913110HCID 53913110, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Dimethylamine hydrochloride (79 mmol) and Boc-L-tyrosine (66 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 12:1 dichloromethane/DMF reaction solvent, 60 hour reaction time) and the product purified by chromatography on silica gel eluted with 10, 20, 30, 50 and 70% ethyl acetate in hexanes. Yield 20.6 g, 102%; HPLC (60/40) 3.21 minutes (96%).

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 10, 20, 30, 50 and 70% ethyl acetate in hexanes
  3. customHPLC (60/40) 3.21 minutes (96%)

Sources & evidence

ORD record
ord-5e591f5e226e42569c28c7a7823c3318
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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