HCID 66949207, compound → HCID 66949959, compound

HRID 1171240Notes

Reaction equation

HRID 1171240 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[C:23]([O:35]CC2C=CC=CC=2)[CH:22]=1)[C:10]([O:12][C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[OH:35][C:23]1[CH:22]=[C:21]([CH2:20][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:10]([O:12][C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])=[O:11])[CH:26]=[CH:25][C:24]=1[OH:27]

Participants

5

Reactant 2

HCID 66949207HCID 66949207, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66949959HCID 66949959, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (1R)-2-acetyloxy-1-methylethyl(2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (18) (12.7 g, 22.1 mmol) in 100 mL of methanol, 10% Pd—C (200 mg) pre-mixed with 10 mL of methanol was added under a nitrogen atmosphere. The nitrogen was exchanged with hydrogen using the evacuation refill cycle method. The mixture was stirred under hydrogen at room temperature for 4 hours. After filtration and washing with methanol, the filtrate was concentrated to afford 8.8 g (100% yield) of the title compound (19). 1H NMR (400 MHz, CDCl3): δ 1.21 (d, J=6.4 Hz, 3H), 1.43 (s, 9H), 2.07 (s, 3H), 2.95 (m, 2H), 4.05 (dd, J=12.0, 6.4 Hz, 1H), 4.12 (dd, J=12.0, 3.2 Hz, 1H), 4.48 (dd, J=14, 6.4 Hz, 1H), 5.04 (d, 1H, NH), 5.15 (m, 1H), 6.53 (d, J=8.0 Hz, 1H), 6.66 (s, 1H), 6.74 (d, J=8.0 Hz, 1H). MS (ESI) m/z 420.0 (M+Na)+ and 396.0 (M−H)−.

Workup

  1. additionwas added under a nitrogen atmosphere
  2. filtrationAfter filtration
  3. washwashing with methanol
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f188267a422947b287a7b0a4a231bb50
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

Loading…