Sodium Carbonate → Carbamic acid, [3-[(cyanomethyl)amino]propyl]-, 1,1-dimethylethyl ester

HRID 2255482Notes

Reaction equation

HRID 2255482 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][C:21]#[N:22]>C(O)C>[CH3:4][C:2]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:20][C:21]#[N:22])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 10560546Carbamic acid, [3-[(cyanomethyl)amino]propyl]-, 1,1-dimethylethyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of (3-aminopropyl)carbamic acid 1,1-dimethylethyl ester (6.00 g, 34 mmol), prepared by the method of Saari et al., J. Med. Chem., 33, 97 (1990), in absolute ethanol (90 mL) was treated with sodium carbonate (3.96 g, 37 mmol) followed by a solution of bromoacetonitrile (2.6 mL, 37 mmol) in ethanol (30 mL) over 45 min. After stirring at room temperature overnight, the contents of the flask were filtered, preadsorbed onto silica gel, and purified by flash chromatography (7 cm diameter, elution with 2.5% methanol in dichloromethane) to afford [3-(cyanomethylamino)propyl]carbamic acid 1,1-dimethylethyl ester as a yellow oil (3.99 g, 55%); IR (neat, cm-1): 3330, 2240, 1700; MS (+CI): 214 (MH+, 20), 187 (76), 158 (100), 131 (44); 1H NMR (CDCl3, 400 MHz): δ 4.80 (br s, NH), 3.61 (s, 2H), 3.22 (q, J=6.5 Hz, 2H), 2.79 (t, J=6.5 Hz, 2H), 1.69 (p, J=6.5 Hz, 2H), 1.45 (s, 9H).

Workup

  1. filtrationthe contents of the flask were filtered
  2. custompurified by flash chromatography (7 cm diameter, elution with 2.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-72e7810556ef4942957817f4c628023f
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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