Triethylamine → 5-[[[4-(Dimethylamino)-1-naphthalenyl]carbonyl]amino]-pentanoic acid methyl ester

HRID 1362574Notes

Reaction equation

HRID 1362574 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=1.ON1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=O.C1(N=C=[N:33][CH:34]2CCCCC2)CCCCC1.C1(/C=C/C=C/[C:50](Cl)=[O:51])C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:50][O:51][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:34][NH:33][C:13]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([N:2]([CH3:1])[CH3:16])=[CH:4][CH:5]=1)=[O:15]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 5226954-(Dimethylamino)-1-naphthoic acidHCID 6450287(2E,4E)-5-phenylpenta-2,4-dienoyl chloride

Product 1

HCID 574954285-[[[4-(Dimethylamino)-1-naphthalenyl]carbonyl]amino]-pentanoic acid methyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(Method J9A) To the mixture of 4-(dimethylamino)-1-naphthalenecarboxylic acid (1/62) (0.32 g, 1.5 mmol) and N-hydroxysuccinimide (0.21 g, 1.8 mmol) in methylene chloride (10 ml), dicyclohexylcarbodiimide (0.37 g, 1.8 mmol) in methylene chloride (2 ml) was added. A white precipitate appeared. The reaction mixture was after 0.5 h filtered through a pad of Celite® into the solution of methyl 5-aminopentanoate hydrochloride (2b) (0.33 g, 1.9 mmol) in methylene chloride, followed by the addition of triethylamine (2.6 ml, 19 mmol). The reaction mixture was stirred at room temperature overnight, evaporated, suspended in water and extracted with 3 portions of ethyl acetate. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed and the residue (0.55 g) was purified on silica gel with light petrol-ethyl acetate (2:1) as eluent to give the title compound (0.31 g, 63%), Rf 0.48 (light petrol-ethyl acetate 1:1). 1H NMR (200 MHz, DMSO-d6, TMS) δ: 1.51-1.59 (4H, m), 2.38 (2H, t, 6.9 Hz), 2.85 (6H, s), 3.26-3.36 (m, overlapped with a signal from DMSO), 3.61 (3H, s), 7.08 (1H, d, 7.6 Hz), 7.48-7.57 (3H, m), 8.15-8.27 (2H, m), 8.43 (1H, t, br).

Workup

  1. additionwas added
  2. customevaporated
  3. extractionextracted with 3 portions of ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed
  7. customthe residue (0.55 g) was purified on silica gel with light petrol-ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-fc1717a97d104caca32e9bb87f9c3b96
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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