Beta-Alanine → HCID 178445780, compound

HRID 2404213Notes

Reaction equation

HRID 2404213 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:22]=O)[CH:18]=3)[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C(O)C.C([BH3-])#N.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:22][NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:18]=3)[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 239Beta-AlanineHCID 311Citric AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 866684172-(4-Tert-butyl-cyclohexyloxy)-quinoline-6-carbaldehyde

Product 1

HCID 178445780HCID 178445780, compoundYield 19.8%

Procedure

A solution of 2-(4-tert-butyl-cyclohexyloxy)-quinoline-6-carbaldehyde (30.6 mg, 0.0983 mmol) and Beta-alanine (8.75 mg, 0.0983 mmol) in ethanol (0.7 mL, 10 mmol) was heated to reflux for 2 h. The yellow solution was cooled to rt and sodium cyanoborohydride (7.41 mg, 0.118 mmol) was added and was heated to reflux for 1 h. After cooled down to rt, citric acid was added and concentrated down. The solid was suspended in water and filtrate, and the collected solid was washed thoroughly with water. HPLC purification of the solid give the product (7.5 mg, 15%). LCMS Rt=1.60 min m/z=385.49 [M+1]. 1H NMR (400 MHz, MeOD) δ=8.14 (d, J=8.8 Hz, 1H), 7.92 (s, 1H), 7.88 (d, J=8.7 Hz, 1H), 7.72 (d, J=10.7 Hz, 1H), 6.96 (d, J=8.8 Hz, 1H), 5.29-5.09 (m, 1H), 4.40 (s, 2H), 3.36 (t, J=5.8 Hz, 2H), 2.79 (t, J=6.7 Hz, 2H), 2.30 (d, J=10.9 Hz, 2H), 1.94 (d, J=12.9 Hz, 2H), 1.55-1.06 (m, 5H), 0.94 (s, 9H).

Workup

  1. temperatureto reflux for 2 h
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooled down to rt
  5. concentrationconcentrated down
  6. washfiltrate, and the collected solid was washed thoroughly with water
  7. customHPLC purification of the solid

Sources & evidence

ORD record
ord-f6cd827e3b22489b8151c772d1b8672e
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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