L-(+)-Cysteine → Fudosteine

HRID 1742751Notes

Reaction equation

HRID 1742751 reaction equation
[Na].[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].Br[CH:10]([OH:13])[CH2:11][CH3:12]>N>[OH:13][CH2:10][CH2:11][CH2:12][S:5][CH2:4][C@@H:3]([C:6]([OH:8])=[O:7])[NH2:2]

Participants

5

Reactant 3

HCID 5862L-(+)-CysteineHCID 5360545SodiumHCID 12887879Bromopropanol

Product 1

HCID 134669FudosteineYield 190.1%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Procedure

The compound was prepared in a similar manner to that described by J. F. Carson, et al, J. Org. Chem., 1964, 29, 2203. To a solution of sodium (6.44 g, 0,281 mol) in liquid ammonia (300 mL) was added cysteine (15.0 g, 62.5 mmol) over a 30 minutes period until permanent discharge of blue. Bromopropanol (15,8 mL, 0.175 mol) was added dropwise over 1 hour. The ammonia was allowed to evaporate and the resulting solid was dissolved in 1M HCl and passed through a column of Dowex 50 (H+) (5×30 cm) eluting with 1N ammonium hydroxide. Lyopholyzation yielded 21.3 g of the title compound as a white solid. MS(CI) m/e 180 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) δ1.70-2.00 (m, 3H), 2.70 (t, J=7.5 Hz, 2H), 3.00-3.21 (m, 3H), 3.58-3.84 (m, 3H), 3.93 (dd, 1H).

Workup

  1. customThe compound was prepared in a similar manner to
  2. customto evaporate
  3. dissolutionthe resulting solid was dissolved in 1M HCl
  4. washeluting with 1N ammonium hydroxide

Sources & evidence

ORD record
ord-3a4060f60aa74d6fac229170182c0677
Source dataset
uspto-grants-1994_08
Patent number
US05340802

Reaction notes

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