Sulfuric Acid → HCID 54003829, compound

HRID 1440517Notes

Reaction equation

HRID 1440517 reaction equation
N[C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4].[Br-:14].[K+].OS(O)(=O)=O.N([O-])=O.[Na+]>O>[Br:14][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 1281066084277-81-6HCID 23668193Sodium Nitrite

Product 1

HCID 54003829HCID 54003829, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-Aminodecanoic acid from Takasago Research Institute (1.5 g., 8.0 mmol) and potassium bromide (3.8 g, 32 mmol) were dissolved in 16 ml of 2.5 m H2SO4 (40 mmol). Slight heating was necessary to the make the reaction homogeneous. The solution was cooled to 0° C. and sodium nitrite (1.1 g, 16 mmol) dissolved in 2 ml water was added dropwise. Brown gas evolved and foaming occurred. The reaction was stirred at 0° C. for 30 minutes and at rt for 2 hours. The reaction was quenched with 100 ml of 5% sodium thiosulfate and extracted with ethyl acetate (3×100 ml). The concentrated organic phase was purified by silica gel column chromatography (eluent: 100% CH2Cl2) to yield 1.2 g (61% yield) of the desired product: [α]20D=-29.9° (c=0.032, MeOH); 1H NMR (CDCl3 δ10.28 (1H, br s), 4.22 (1H, t, J=7.4 Hz), 2.02 (2H, m), 1.26 (12H, m), 0.87 (3H, t, J=6.8 Hz).

Workup

  1. temperatureSlight heating
  2. additionwas added dropwise
  3. customThe reaction was quenched with 100 ml of 5% sodium thiosulfate
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. customThe concentrated organic phase was purified by silica gel column chromatography (eluent: 100% CH2Cl2)

Sources & evidence

ORD record
ord-a01a37426f4e45b6873e9bb840eebae5
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

Loading…