N-Methylisopropylamine → HCID 68839959, compound

HRID 660595Notes

Reaction equation

HRID 660595 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][C:31]([OH:33])=O)[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]1(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.[CH:56]([NH:59][CH3:60])([CH3:58])[CH3:57]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][C:31]([N:59]([CH:56]([CH3:58])[CH3:57])[CH3:60])=[O:33])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[S:16]1(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78485N-MethylisopropylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68839806HCID 68839806, compound

Product 1

HCID 68839959HCID 68839959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid (0.10 g, 0.2 mmol), EDCl (0.38 g, 0.20 mmol) and HOAt (0.027 g, 0.20 mmol) in DMF (1 mL) is added N-isopropyl-N-methylamine (0.15 g, 0.2 mmol). The mixture is stirred at RT for 18 h, then poured into water. The mixture is extracted into EtOAc and the organic phase washed with water (3×) and sat. NaCl (1×). The organic solution is dried over Na2SO4 and the solvent removed under reduced pressure to afford the title compound. This is used directly in the next step.

Workup

  1. extractionThe mixture is extracted into EtOAc
  2. washthe organic phase washed with water (3×) and sat. NaCl (1×)
  3. dry with materialThe organic solution is dried over Na2SO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ef80907231c24a9aa6f7a95532699983
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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