Dichloromethane → HCID 53979746, compound

HRID 53940Notes

Reaction equation

HRID 53940 reaction equation
[N:1]([C@@:4]([C:9]([OH:11])=[O:10])([CH:6]([CH3:8])[CH3:7])N)=[C:2]=[O:3].[CH3:12][N:13]([C:15]1[S:16][CH:17]=[C:18]([CH2:20][NH:21][CH3:22])[N:19]=1)[CH3:14].Cl[CH2:24]Cl>>[CH3:24][O:11][C:9](=[O:10])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:1][C:2]([N:21]([CH3:22])[CH2:20][C:18]1[N:19]=[C:15]([N:13]([CH3:12])[CH3:14])[S:16][CH:17]=1)=[O:3]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 187589612-(N,N-dimethylamino)-4-(((N-methyl)amino)methyl)thiazoleHCID 22856914alpha-isocyanato-L-valine

Product 1

HCID 53979746HCID 53979746, compoundYield 34%

Procedure

A solution of 741 mg (4.42 mmol) of α-isocyanato-L-valine in in 5 ml of dichloromethane was added to a solution of 720 mg (4.21 mmol) of 2-(N,N-dimethylamino)-4-(((N-methyl)amino)methyl)thiazole in 25 ml of dichloromethane. The resulting solution was stirred at ambient temperature for 16 h, partitioned between chloroform and aqueous NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 463 mg (34%) of the desired compound, Rf 0.25 (2% methanol in chloroform). NMR (CDCl3) δ 0.96 (d, J=7 Hz, 3 H), 0.98 (d, J=7 Hz, 3 H), 2.13 (m, 1 H), 2.97 (s, 3 H), 3.11 (s, 6 H), 3.71 (s, 3 H), 4.07 (br d, J=16 Hz, 1 H), 4.34 (dd, J=9, 5 Hz, 1 H), 4.42 (d, J=16 Hz, 1 H), 6.29 (s, 1 H), 6.37 (br, 1 H). Mass spectrum: (M+H)+ =329.

Workup

  1. custompartitioned between chloroform and aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-555b21551cd340e588db4bb6b56eb18b
Source dataset
uspto-grants-1997_04
Patent number
US05621109

Reaction notes

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