Sodium Cyanide → 7-Cyano-5-(hydroxymethyl)-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylic acid

HRID 1906245Notes

Reaction equation

HRID 1906245 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][N:5]1[C@H:9]2[C@H:10]3[N:15]4[C@H:16]([O:17][CH2:18][C@H:14]4[C:13]4[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:12]=4[CH2:11]3)[C@@H:6]1[CH2:7][C@H:8]2[C:25]([O-:27])=[O:26]>P([O-])([O-])([O-])=O>[CH3:4][N:5]1[CH:9]2[CH:10]3[N:15]([CH:16]([C:1]#[N:2])[CH:6]1[CH2:7][CH:8]2[C:25]([OH:27])=[O:26])[CH:14]([CH2:18][OH:17])[C:13]1[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:12]=1[CH2:11]3

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 91820461HCID 91820461, compound

Product 1

HCID 1227377-Cyano-5-(hydroxymethyl)-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-epiminoazepino[1,2-b]isoquinoline-10-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

At first, 2.0 g of sodium cyanide is dissolved in 30 ml of 0.1M phosphate buffer (pH 7.4) and 1 g of crude DC-52-(containing 0.6 g of DC-52) is added thereto. The mixture is stirred at room temperature for 1.5 hours. The reaction mixture is passed through a column containing 200 ml of Diaion HP-20SS (made by Mitsubishi Chemical Industries Co., Ltd.), and the column is developed and eluted with 1 l of water (fraction Nos. 1-160; 6 ml each), and then with 1% acetone-99% water (by volume; fraction Nos. 161-224, 6 ml each). Fraction Nos. 125-165 and fraction Nos. 166-199 are joined together separately, and concentrated under reduced pressure, followed by freeze-drying to obtain 161 mg of fraction A and 179 mg of fraction B.

Workup

  1. additioncontaining 200 ml of Diaion HP-20SS (made by Mitsubishi Chemical Industries Co., Ltd.)
  2. washeluted with 1 l of water (fraction Nos. 1-160; 6 ml each)
  3. concentrationconcentrated under reduced pressure
  4. customby freeze-drying
  5. customto obtain 161 mg of fraction A and 179 mg of fraction B

Sources & evidence

ORD record
ord-65cfa3f841c94b94af2439fd2f401c9b
Source dataset
uspto-grants-1987_03
Patent number
US04650869

Reaction notes

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