N-Methylaniline → HCID 31774563, compound

HRID 2082216Notes

Reaction equation

HRID 2082216 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([N:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:20])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 31774563HCID 31774563, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-Phe-OH (2.65 g), N-methylaniline (1.09 g) and HOBT (1.35 g) in DMF (25 ml) was added WSC.HCl (1.92 g) under ice-cooling. The mixture was stirred for 5 hours at room temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water and saturated sodium chloride solution, and dried over magnesium sulfate. The evaporated residue was subjected to column chromatography on silica gel (100 g) and eluted with a mixture of chloroform and methanol (100:1). The fractions containing the object compound were combined and evaporated to give Boc-Phe-NMePh (2.17 g).

Workup

  1. temperaturecooling
  2. customAfter evaporation and extraction with ethyl acetate
  3. washthe organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. washeluted with a mixture of chloroform and methanol (100:1)
  6. additionThe fractions containing the object compound
  7. customevaporated

Sources & evidence

ORD record
ord-06a5228da9fc44b8a5f7a93bcf9d8682
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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