HCID 53248046, compound → 4-Azido-2-sulfobutanoic acid

HRID 1914440Notes

Reaction equation

HRID 1914440 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([S:11]([OH:14])(=[O:13])=[O:12])[C:7]([O:9]C)=[O:8])=[N+:2]=[N-:3]>Cl>[N:1]([CH2:4][CH2:5][CH:6]([S:11]([OH:14])(=[O:12])=[O:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 53248046HCID 53248046, compound

Product 1

HCID 532480474-Azido-2-sulfobutanoic acidYield 117.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-azido-2-sulfo-butyrate (1.00 g, 4.08 mmol) in the mixture of HCl (50 ml, 1.0 M) and HAC (5 ml) was heated at 100° C. for 8 hrs. The mixture was evaporated and co-evaporated 3×50 ml of water, and crystallized with water/acetone to afford 1.0 g (99%) of the title compound. 1H NMR (DMF-d7): 3.60 (m, 2H), 3.52 (m, 1H), 2.24 (m, 2H). 13C NMR 170.96, 63.04, 50.66, 29.12. ESI MS m/z− 207.7 (MW−H); HRMS m/z− (C4H7N3O5S—H) calcd 208.0028. found 208.0021.

Workup

  1. customThe mixture was evaporated
  2. customco-evaporated 3×50 ml of water, and crystallized with water/acetone

Sources & evidence

ORD record
ord-583321936d5b4e57869207429f03f89f
Source dataset
uspto-grants-2013_12
Patent number
US08613930B2

Reaction notes

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