1956-23-6 → HCID 19003131, compound

HRID 2259298Notes

Reaction equation

HRID 2259298 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH:7]([C:9](O)=[O:10])[NH2:8])[C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[S:1]1[CH:5]=[C:4]([CH2:6][CH:7]([NH2:8])[CH2:9][OH:10])[C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]1=2

Participants

4

Reactant 2

HCID 4270761956-23-6HCID 21226445Aluminium lithium hydride

Product 1

HCID 19003131HCID 19003131, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of β-(3-benzo[b]thienyl)DL alanine (5.0 g) [P. N. Rao et al, Int. J. Peptide Protein Res, 29, 118, (1987)] in dry tetrahydrofuran (50 ml) was added to an ice cold solution of lithium aluminium hydride in dry tetrahydrofuran (22 ml of a 1M solution). Once addition was complete the mixture was warmed to reflux for one hour, cooled to room temperature and the reaction quenched by the addition of 4N sodium hydroxide (5.0 ml). The reaction mixture was diluted with water (100 ml) extracted with ethyl acetate (2×100 ml), the organic layers were separated, dried (MgSO4), filtered and the solvent removal under reduced pressure to afford the title compound as a colourless oil. 1H NMR (360 MHz, CDCl3) δ2.65 (1H, m, CH2CHCH2OH), 2.99 (2H, m, CH2CH2OH), 3.23 (2H, m, CH2CHCH2OH), 7.44 (2H, m, 2×ArH), 7.61 (1H, s, S-CHC), 7.86 (1H, dd, J=6.0, 1.0 Hz, ArH), 7.97 (1H, dd, J=6.0, 1.0 Hz, ArH). m/z (EI+) 207.

Workup

  1. additionOnce addition
  2. temperaturewas warmed
  3. temperatureto reflux for one hour
  4. customthe reaction quenched by the addition of 4N sodium hydroxide (5.0 ml)
  5. additionThe reaction mixture was diluted with water (100 ml)
  6. extractionextracted with ethyl acetate (2×100 ml)
  7. customthe organic layers were separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removal under reduced pressure

Sources & evidence

ORD record
ord-94c56b4381ca462fb7218f06906bb6de
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

Loading…