Chloride → HCID 13232653, compound

HRID 638128Notes

Reaction equation

HRID 638128 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.[Cl-].[C-:31]#[N:32].[K+]>C(Cl)(Cl)(Cl)Cl.O>[C:31]([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:32]

Participants

6

Reactant 3

HCID 312ChlorideHCID 9032Potassium CyanideHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

Product 1

HCID 13232653HCID 13232653, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 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-octlymethylammonium 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-d55b9419de4344d692e060db053a9317
Source dataset
uspto-grants-1985_12
Patent number
US04560508

Reaction notes

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