Water → HCID 20029138, compound

HRID 868184Notes

Reaction equation

HRID 868184 reaction equation
[OH-:1].[Na+].[S:3]([N:13]1[CH2:16][C:15]([CH2:19][OH:20])([CH2:17][OH:18])[CH2:14]1)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].BrBr.[OH2:23]>[Ni](Cl)Cl>[S:3]([N:13]1[CH2:14][C:15]([C:19]([OH:23])=[O:20])([C:17]([OH:1])=[O:18])[CH2:16]1)([C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 21287788HCID 21287788, compound

Product 1

HCID 20029138HCID 20029138, compound

Reagents, catalysts & solvents 1

HCID 24385Nickel DichlorideCatalyst

Procedure

Sodium hydroxide (6.3 g) was dissolved in water (50 ml) and nickel chloride (1 g) and N-tosyl-3,3-bis(hydroxymethyl)azetidine (4.4 g) were added. Bromine (9.6 g) was added over 6 hours to the green suspension with vigorous stirring and cooling. The mixture was stirred overnight and the last traces of nickel peroxide destroyed with sodium sulphite. The green precipitate was filtered off and the clear filtrate acidified to pH 1 with hydrochloric acid. Ether extraction yielded the desired product, N-tosylazetidine-3,3-dicarboxylic acid.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred overnight
  3. customthe last traces of nickel peroxide destroyed with sodium sulphite
  4. filtrationThe green precipitate was filtered off
  5. extractionEther extraction

Sources & evidence

ORD record
ord-c51bf85d3b364717924a33cb900c1487
Source dataset
uspto-grants-1988_10
Patent number
US04778577

Reaction notes

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