Sodium Azide → [(2-Azido-3-methoxy-3-oxopropyl)sulfanyl]acetic acid

HRID 1248269Notes

Reaction equation

HRID 1248269 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](Cl)[CH2:5][S:6][CH2:7][C:8]([OH:10])=[O:9].[N-:13]=[N+:14]=[N-:15].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:1][O:2][C:3](=[O:12])[CH:4]([N:13]=[N+:14]=[N-:15])[CH2:5][S:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14189835[(2-Chloro-3-methoxy-3-oxopropyl)sulfanyl]acetic acid

Product 1

HCID 14189839[(2-Azido-3-methoxy-3-oxopropyl)sulfanyl]acetic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

1.00 gram (4.70 mmoles) of the 2-chloro-3-carboxymethylmercapto-propionic acid methyl ester produced in Example 9 was stirred with 0.46 gram (7.08 mmoles) of sodium azide and 0.10 gram of Aliquat 336 in 2 ml of water for 15 hours at 50° C. After working up according to Example 2 there were obtained 0.91 gram (88% of theory) of 2-azido-3-carboxymethylmercapto-propionic acid methyl ester as an analytically pure material.

Sources & evidence

ORD record
ord-d09fea13d881443b8b59d4adc3c289f8
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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