Propamine → N-(p-nitrobenzyloxycarbonyl)-1-amino-2-propanethiol

HRID 981854Notes

Reaction equation

HRID 981854 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].[NH2:15][CH2:16][CH:17]([SH:19])[CH3:18].C([O-])(O)=O.[Na+]>CCOCC.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][C:2]([NH:15][CH2:16][CH:17]([SH:19])[CH3:18])=[O:3])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 11717PropamineHCID 782054-Nitrobenzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 13175758N-(p-nitrobenzyloxycarbonyl)-1-amino-2-propanethiolYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of p-nitrobenzyl chloroformate (0.95 g, 4.41 mmol) in Et2O (30 ml) was added dropwise over 45 min. to an ice-cold, stirring mixture of 1-amino-2-propanethiol (0.504 g, 3.94 mmol) in Et2O (100 ml), H2O (11 ml), and 10% aqueous NaHCO3 (10 ml). The resulting mixture was stirred an additional 80 min. at 0°-5°, and then separated into two phases. The organic portion was washed with cold 0.025N HCl (30 ml) and brine (20 ml), dried with MgSO4, filtered, and concentrated under vacuum to a yellow oil (1.28 g). The crude product was purified by preparative TLC on silica gel GF using 20:1 CH2Cl2 -EtOAc as developing solvent to afford an off-white solid (1.00 g). Recrystallization of the chromatographed product from Et2O-petroleum ether gave compound (A3) (0.183 g) as a cream colored solid: mp 54°- 56.5°.

Workup

  1. stirringThe resulting mixture was stirred an additional 80 min. at 0°-5°
  2. customseparated into two phases
  3. washThe organic portion was washed with cold 0.025N HCl (30 ml) and brine (20 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum to a yellow oil (1.28 g)
  7. customThe crude product was purified by preparative TLC on silica gel

Sources & evidence

ORD record
ord-f8c0b279618c46c6a250e8a50a1601b1
Source dataset
uspto-grants-1991_02
Patent number
US04992542

Reaction notes

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