Beta-Alanine → HCID 66822401, compound

HRID 2406563Notes

Reaction equation

HRID 2406563 reaction equation
NCCC(O)=O.[NH:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=O.[C:14]([CH2:16][C:17]([NH:19][CH:20]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:26][CH:25]=1)[CH2:21][CH2:22][CH3:23])=[O:18])#[N:15]>C(O)C.O.CCOC(C)=O.CCCCCC>[C:14](/[C:16](=[CH:12]\[C:8]1[NH:7][CH:11]=[CH:10][N:9]=1)/[C:17]([NH:19][CH:20]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:28][CH:29]=1)[CH2:21][CH2:22][CH3:23])=[O:18])#[N:15]

Participants

6

Reactant 3

HCID 239Beta-AlanineHCID 249551H-imidazole-2-carbaldehydeHCID 66822001HCID 66822001, compound

Product 1

HCID 66822401HCID 66822401, compoundYield 155.2%

Reagents, catalysts & solvents 2

HCID 19096565Water ethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

β-Alanine (71.3 mg, 0.8 mmol) and 1H-imidazole-2-carbaldehyde (19.2 mg, 0.2 mmol) were added successively to a stirred solution of 2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acetamide (5; 27.6 mg, 0.1 mmol) in ethanol/water (2.0 mL/0.8 mL) at room temp. After 72 hours TLC (in 50% EtOAc/Hexane) showed a single product formed. The mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The separated organic layer was washed with sat. brine and dried with sodium sulfate and concentrated to give a light amber oil (55 mg) as crude product. The crude material was purified by column chromatography to afford the titled compound as a yellow oil (23 mg) in 65% yield. 1H NMR (500 MHz, CDCl3) δ 10.59 (s, 1H), 8.14 (s, 1H), 7.42 (s, 1H), 7.23 (s, 1H), 7.17-7.13 (m, 2H), 7.12-7.07 (m, 2H), 5.22 (s, 2H), 3.86-3.75 (m, 2H), 3.51 (s, 3H), 1.64-1.53 (m, 2H), 1.36 (m, 2H), 0.93 (t, J=7.3, 3H). Mass spec ES+, m/z=355.1 (m+H+).

Workup

  1. customa single product formed
  2. customThe mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washThe separated organic layer was washed with sat. brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96666b0520324ababd7ebdb918c3557b
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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