Hydrochloric Acid → HCID 14196781, compound

HRID 1362570Notes

Reaction equation

HRID 1362570 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)=[O:11].[Li+].[OH-].Cl>O1CCCC1>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:22])=[O:2])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9221044HCID 9221044, compound

Product 1

HCID 14196781HCID 14196781, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Method J5B) The crude 6-[(naphthalene-2-carbonyl)amino]hexanoic acid methyl ester (3/53) was dissolved in tetrahydrofuran (5 ml) and 1N LiOH (5.5 ml, 5 mmol) was added. The reaction mixture was stirred for three hours at room temperature and acidified with 2N HCl up to pH 3. The mixture was extracted with ethyl acetate (3×20 ml) the organic layer was washed with saturated NaCl (3×10 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel with ethyl acetate as eluent to give pure title compound (0.618 g, 79%). 1H NMR (CDCl3, HMDSO), δ: 1.11-1.77 (6H, m); 2.22-2.39 (2H, m); 3.47 (2H, dd, J=7.0 Hz); 6.26 (1H, br s); 7.17 (1H, s); 7.33-7.57 (2H, m); 7.64-7.93 (4H, m); 8.22 (1H, s).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×20 ml) the organic layer
  2. washwas washed with saturated NaCl (3×10 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed on silica gel with ethyl acetate as eluent

Sources & evidence

ORD record
ord-f57a676b498045b0a0e23da0ef15ad7a
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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