Water → HCID 67411816, compound

HRID 709899Notes

Reaction equation

HRID 709899 reaction equation
[NH2:1][C:2]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=2)([CH3:6])[C:3](O)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.CC(=O)OCC>C1COCC1>[NH2:1][C:2]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=2)([CH3:6])[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 67410593HCID 67410593, compound

Product 1

HCID 67411816HCID 67411816, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-amino-2-(7-(heptyloxy)quinolin-3-yl)propanoic acid (600 mg, 1.8 mmol) in dry THF (30 mL) was added LAH (138 mg, 3.6 mmol, 2 eq.) at 0° C. under N2. The mixture was warmed to room temperature for 3 h. Then to the reaction mixture was added water (1 mL), diluted (EA), filtered and dried (Na2SO4), evaporated to dryness to give the crude product, which was purified by prep-HPLC to give desired compound as white solid (200 mg, yield 35%). ESI-MS: 317 (M+H)+. 1H NMR (300 MHz, CDCl3) δ: 0.90 (t, 3H), 1.32-1.42 (m, 6H), 1.48-1.52 (m, 2H), 1.53 (s, 3H), 1.82-1.89 (m, 2H), 2.34 (brs, 3H), 3.66-3.69 (d, 1H), 3.81-3.84 (d, 1H), 4.08 (t, 2H), 7.11-7.14 (m, 1H), 7.26 (s, 1H), 7.57-7.59 (d, 1H), 8.10 (s, 1H), 8.83 (s, 1H). HPLC: 214 nm: 98.948%, 254 nm: 99.526%.

Workup

  1. filtrationfiltered
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness
  4. customto give the crude product, which
  5. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-c6a76593603643a99a6b2316fb8b616e
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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