Water → N-Boc-D-Homophenylalanine Quinoline-3-amide

HRID 1359906Notes

Reaction equation

HRID 1359906 reaction equation
[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N[C:22]1[CH:23]=[N:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.C1(N=C=NC2CCCCC2)CCCCC1.O>C(OCC)(=O)C.C(O)(=O)C.C(N(CC)CC)C.C(#N)C>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[C:22]([C:1]([NH2:8])=[O:2])[CH:23]=1.[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

9

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 113753-AminoquinolineHCID 2755954Boc-D-homophenylalanine

Product 1

HCID 66963140N-Boc-D-Homophenylalanine Quinoline-3-amideYield 178%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-Boc-D-Homophenylalanine (3.0 g, 10.7 mmol) in ethyl acetate (100 mL) was treated with 3-aminoquinoline (3.08 g, 21.4 mmol) followed by dicyclohexylcarbodiimide (2.31 g, 11.2 mmol). The reaction was stirred at 25° C. for 3 hr (HPLC monitoring RP-18, 250×4 mm, water:acetonitrile:triethylamine:acetic acid=500:500:0.6:1 (mL), UV detector, λ=254 nm), filtered and the filtrate washed with 1M hydrochloric acid (25 mL), saturated solution of sodium bicarbonate (25 mL) and water (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford title compound (4.3 g) as white solid.

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with 1M hydrochloric acid (25 mL), saturated solution of sodium bicarbonate (25 mL) and water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-39aa9e24f7e84195a14046e3d62cd544
Source dataset
uspto-grants-2011_02
Patent number
US07879795B2

Reaction notes

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