2-Naphthylalanine → HCID 69654546, compound

HRID 1244001Notes

Reaction equation

HRID 1244001 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH2:6][CH:7](Br)[CH3:8].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:4]1[CH2:5][CH2:6][C@@H:7]([CH3:8])[NH:17][C@H:10]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:18]

Participants

5

Reactant 3

HCID 1859152-NaphthylalanineHCID 516892Sodium BicarbonateHCID 69655081HCID 69655081, compound

Product 1

HCID 69654546HCID 69654546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(A mixture of two diastereomers and their enantiomers.) To 2-(amino-phenyl-methyl)-5-bromo-hexanoic acid methyl ester in DMF was added Nal and NaHCO3 The resultant mixture was stirred in DMF at 100° C. for 1 hour, and then was cooled to room temperature and partitioned between ether and water. The organic layer was washed with brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography (97:3 CHCl3/MeOH) gave 1.63 g (90%) of the the product as an inseparable mixture of two diastereomers. 1H NMR (400 MHz, CDCl3) δ 7.17–7.32 (comp, 10H, both diastereomers), 4.47 (d, J=5.0 Hz, 1H), 3.97 (d, J=3.5 Hz, 1H), 3.45 (s, 3H), 3.38 (s, 3H), 3.02–3.08 (m, 1H), 2.92–2.99 (m, 1H), 2.75–2.85 (comp, 2H), 2.0–2.2 (comp, 2H), 1.80–2.00 (comp, 3H), 1.40–1.60 (comp, 2H), 1.20–1.30 (m, 1H), 1.20 (d, J=6.4 Hz, 3H), 1.07 (d, J=6.4 Hz, 3H); Mass spectrum m/e calcd. for M+H=234.1. Found 234.2.

Workup

  1. addition(A mixture of two diastereomers and their enantiomers
  2. custompartitioned between ether and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customSilica gel chromatography (97:3 CHCl3/MeOH) gave 1.63 g (90%) of the the product
  8. additionas an inseparable mixture of two diastereomers

Sources & evidence

ORD record
ord-eebad9b10cd34403b45f39b7d89e3814
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…