Potassium Cyanide → HCID 13232653, compound

HRID 1788803Notes

Reaction equation

HRID 1788803 reaction equation
CS([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)=O.[C-:30]#[N:31].[K+]>C(Cl)(Cl)(Cl)Cl.[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.O>[C:30]([CH:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:31]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

Product 1

HCID 13232653HCID 13232653, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

In 120 ml of carbon tetrachloride are dissolved 12.2 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone and 2.44 g of tri-n-octylmethylammonium chloride and, under stirring, a solution of 2.15 g of potassium cyanide in 30 ml of water is added. The mixture is stirred vigorously at the same temperature for 15 minutes and the organic layer is separated, while the aqueous layer is extracted with chloroform. The organic layers are combined, washed with water and treated in the same manner as (1) of Example 13 to give 7.66 g of (3S,4RS)-4-cyano-3-tritylamino-2-azetidinone.

Workup

  1. stirringThe mixture is stirred vigorously at the same temperature for 15 minutes
  2. customthe organic layer is separated, while the aqueous layer
  3. extractionis extracted with chloroform
  4. washwashed with water
  5. additiontreated in the same manner as (1) of Example 13

Sources & evidence

ORD record
ord-98f46b24b7374845b869dde97ca1bcc2
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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