Ethyl 3-isocyanatobenzoate → HCID 21459767, compound

HRID 1941096Notes

Reaction equation

HRID 1941096 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]=[O:3].[NH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C>[C:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][CH2:16][NH:15][C:2](=[O:3])[NH:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 589806Ethyl 3-isocyanatobenzoateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 21459767HCID 21459767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.00 g (8.12 mmol) of ethyl 3-isocyanatobenzoate (78%) are dissolved in 10 ml of DMF..A solution of 1.42 g (8.12 mmol) of 1-amino-3-tert-butyloxycarbonylaminopropane in 20 ml of DMF is slowly added dropwise at 2°-8°C. After stirring at room temperature for 2 h, the solvent is removed in vacuo, and the residue is treated with ethyl acetate and the mixture is washed with water. After drying (MgSO4), solid is filtered off and the solvent is removed in vacuo. The residue is chromatographed on silica gel.

Workup

  1. customthe solvent is removed in vacuo
  2. additionthe residue is treated with ethyl acetate
  3. washthe mixture is washed with water
  4. dry with materialAfter drying (MgSO4), solid
  5. filtrationis filtered off
  6. customthe solvent is removed in vacuo
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-7839a1926b8c4590a805f01b2e514605
Source dataset
uspto-grants-1997_12
Patent number
US05703050

Reaction notes

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