HCID 21919498, compound → HCID 86586422, compound

HRID 1244533Notes

Reaction equation

HRID 1244533 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([O:22][CH3:23])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[O:24]=[C:25]1[C:28]2([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:27](O)=[CH:26]1>C(Cl)Cl>[O:24]=[C:25]1[C:28]2([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:27]([NH:1][C@@H:2]([CH2:7][C:8]2[CH:9]=[C:10]([O:22][CH3:23])[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([O:14][CH3:15])[CH:13]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:26]1

Participants

4

Reactant 2

HCID 21919498HCID 21919498, compoundHCID 68807255HCID 68807255, compound

Product 1

HCID 86586422HCID 86586422, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2S)-2-amino-3-(2,6-dimethoxy[1,1′-biphenyl]-4-yl)propanoate (0.80 g, 2.5 mmol) in DCM (10 ml) at room temperature was added 1-keto-3-hydroxyspiro[3,5]-non-2-ene (0.38 g, 2.5 mmol) and the mixture stirred for 48 h. Volatiles were removed in vacuo and the residue purified by column chromatography (SiO2, EtOAc) to give the title compound as a white solid (1.05 g, 92%). δH (CDCl3): 7.32–7.26 (3H, m), 7.12 (2H, d, J 8.2 Hz), 6.92 (2H, d, J 8.3 Hz), 5.90 (1H, br d, J 8.2 Hz), 4.60 (1H, s), 4.33 (1H, br), 3.86 (3H, s), 3.73 (6H, s), 3.30 (1H, dd, J 13.9, 5.3 Hz), 3.13 (1H, dd, J 13.9, 6.3 Hz), 1.82–1.33 (10H, m); m/z (ES+, 70V) 450.1 (MH+).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue purified by column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-a5e1ff5e674c49b79a88d7a1c9c7da6c
Source dataset
uspto-grants-2006_10
Patent number
US07122556B2

Reaction notes

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