Hydrochloric Acid → HCID 14275194, compound

HRID 2066364Notes

Reaction equation

HRID 2066364 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH3:10][N:11]([CH3:26])[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[C:17]2[S:22](Cl)(=[O:24])=[O:23].Cl>C([O-])(O)=O.[Na+].CC(C)=O.C(N(CC)CC)C>[CH3:10][N:11]([CH3:26])[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[C:17]2[S:22]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:24])=[O:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 11801Dansyl chloride

Product 1

HCID 14275194HCID 14275194, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 6-aminohexanoic acid (1.5 g, 11.4 mmol) in 1 M NaHCO3 (45 as added 5-(dimethylamino)naphthalene-1-sulfonyl chloride (0.63 g, 2.33 mmol) in acetone (10 mL) and triethylamine (2 mL). The solution was stirred for 1 h, acidified to pH 3 with 2 N HCl, extracted with ethyl acetate (3×15 mL). The organic layer was washed with water (15 mL) and brine (15 mL), dried over Na2SO4. The solvent was evaporated and purified by flash chromatography using CH2Cl2-MeOH to afford 6-(5-dimethylaminonaphthalene-1-sulfonamido)hexanoic acid as a green sticky oil (0.76 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 10.66 (br, 1H), 8.46 (d, 1H, J=8.4 Hz), 8.33 (d, 1H, J=8.4 Hz), 8.19 (d, 1H, J=7.2 Hz), 7.44 (m, 2H), 7.09 (d, 1H, J=7.6 Hz), 5.66 (br, 1H), 2.85 (m, 2H), 2.79 (s, 6H), 2.08 (t, 2H, J=8.8, 7.6 Hz), 1.32 (m, 4H), 1.12 (m, 2H); 13C NMR (100 MHz) δ 179.29, 151.67, 135.03, 130.18, 129.72, 129.58, 129.25, 128.26, 123.16, 119.01, 115.20, 45.30, 42.88, 33.98, 29.07, 25.74, 24.01.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe organic layer was washed with water (15 mL) and brine (15 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-68645eadfdb943d1965c2238e5e66f4d
Source dataset
uspto-grants-2012_10
Patent number
US08293513B2

Reaction notes

Loading…