Potassium Cyanide → HCID 13232653, compound

HRID 1788805Notes

Reaction equation

HRID 1788805 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+]>C1C=CC=CC=1.CCCCC[N+](CCCCC)(CCCCC)CCCCC.[Br-].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, compound

Reagents, catalysts & solvents 3

HCID 70086866-97-7CatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

In 2 ml of benzene are dissolved 0.5 mmol of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone and 0.1 mmol of tetra-n-amylammonium bromide, and a solution of 0.55 mmol of potassium cyanide in 0.55 ml of water is added at 15° C. The mixture is stirred vigorously for 15 minutes and treated in the same manner as Example 20 to give (3S,4RS)-4-cyano-3-tritylamino-2-azetidinone with the (3S,4R):(3S,4S) ratio of 1:4.

Workup

  1. additiontreated in the same manner as Example 20

Sources & evidence

ORD record
ord-ae461d73bcff45228281b4f8a3db474f
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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