(-)-(R)-N-((R)-2-hydroxy-1-phenylethyl)-2-methyl-5-phenylpentanamide → (2R)-5-Phenyl-2-methylpentanoic acid

HRID 709111Notes

Reaction equation

HRID 709111 reaction equation
OC[C@H](NC(=O)[C@H](C)CCCC1C=CC=CC=1)C1C=CC=CC=1.[CH3:24][C@@H:25]([CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]([OH:28])=[O:27]>>[CH3:24][C@H:25]([CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]([OH:28])=[O:27]

Participants

3

Reactant 2

HCID 90025591(-)-(R)-N-((R)-2-hydroxy-1-phenylethyl)-2-methyl-5-phenylpentanamideHCID 90054467(S)-2-methyl-5-phenylpentanoic acid

Product 1

HCID 12153395(2R)-5-Phenyl-2-methylpentanoic acid

Procedure

-(−)-2-Methyl-5-phenylpentanoic acid was prepared from 19mc(i) (30 g) in the same manner (S)-(+)-2-methyl-5-phenylpentanoic acid was prepared from 19mb(i) as described above. The residue was purified by silica gel chromatography. Elution with ethyl acetate-heptane-acetic acid (20:80:0.4 v/v/v) afforded the title compound (20.8 g) as a clear oil; TLC Rf 0.51 (solvent system: 30:70:1 v/v/v ethyl aceate-hepatane-acetic acid; HPLC retention time 24.46 min; Chiralpak IA 4.6×25 mm 5μ, at a wavelength of 208 nm 0.75 mL/min, 99:1:0.5 heptane: 2-propanol: acetic acid, chiral purity 99.32% (R), 0.68% (S); MS (ESI−) m/z 191.1 (M−H)−; 1H-NMR (CDCl3) δ 7.31-7.26 (m, 2H), 7.21-7.15 (m, 3H), 2.67-2.57 (m, 2H), 2.54-2.44 (m, 1H), 1.79-1.59 (m, 3H) 1.58-1.41 (m, 1H), 1.18 (d, J=6.96 Hz, 3H).

Workup

  1. customwas prepared from 19mb(i)
  2. customThe residue was purified by silica gel chromatography
  3. washElution with ethyl acetate-heptane-acetic acid (20:80:0.4 v/v/v)

Sources & evidence

ORD record
ord-3b84c53d10034031b3b1d3c708c3356e
Source dataset
uspto-grants-2015_11
Patent number
US09180116B2

Reaction notes

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