Diisopropylethylamine → Methyl 2-(4-{[3-(4-amino-1-naphthyl)propanoyl]amino}butoxy)-6-hydroxybenzoate

HRID 488669Notes

Reaction equation

HRID 488669 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:4][CH:3]=1.Cl.[CH3:18][O:19][C:20](=[O:34])[C:21]1[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][C:22]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33].F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]([NH:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([OH:27])[C:21]=2[C:20]([O:19][CH3:18])=[O:34])=[O:16])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 222719303-(4-Amino-1-naphthyl)propanoic acidHCID 69597617Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate hydrochloride

Product 1

HCID 22271961Methyl 2-(4-{[3-(4-amino-1-naphthyl)propanoyl]amino}butoxy)-6-hydroxybenzoateYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-amino-1-naphthyl)propanoic acid (160 mg, 0.74 mmol), 2-(4-amino-butoxy)-6-hydroxy-benzoic acid methyl ester hydrochloride (200 mg, 0.72 mmol), [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium tetrafluoroborate (TBTU) (275 mg, 0.857 mmol) and N,N-diisopropylethylamine (0.4 mL, 2.3 mmol) in DMF (3 mL) was stirred at ambient temperature for 1.5 hour, poured into water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate layers were washed with water (2×5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to an oil. The product was purified on silica gel, eluting with 75% ethyl acetate/hexanes to provide the titled compound (165 mg, 52%).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined ethyl acetate layers were washed with water (2×5 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to an oil
  6. customThe product was purified on silica gel
  7. washeluting with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb2c83115b8844f9a7465bd3c1cf3092
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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