HCID 86621600, compound → HCID 86621601, compound

HRID 2233797Notes

Reaction equation

HRID 2233797 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28]CC2C=CC=CC=2)=[C:24]([O:36]CC2C=CC=CC=2)[CH:23]=1)[C:10]([O:12][C@H:13]([CH3:20])[C@H:14]([O:16][C:17](=[O:19])[CH3:18])[CH3:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[OH:36][C:24]1[CH:23]=[C:22]([CH2:21][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]([O:12][C@H:13]([CH3:20])[C@H:14]([O:16][C:17](=[O:19])[CH3:18])[CH3:15])=[O:11])[CH:27]=[CH:26][C:25]=1[OH:28]

Participants

5

Reactant 2

HCID 86621600HCID 86621600, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86621601HCID 86621601, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (1R,2R)-2-acetyloxy-1-methylpropyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (7) (2.0 g, 3.4 mmol) in 20 mL of methanol, 10% Pd—C (100 mg) pre-mixed with 10 mL of methanol was added under nitrogen atmosphere. The nitrogen was exchanged with hydrogen and the mixture stirred under the hydrogen atmosphere at room temperature for 4 h. After filtration and washing with methanol, the filtrate was concentrated to provide 1.4 g (100% yield) of the title compound (8). 1H NMR (400 MHz, CDCl3): δ 1.14 (d, J=6.4 Hz, 3H), 1.16 (d, J=6.4 Hz, 3H), 1.42 (s, 9H), 2.06 (s, 3H), 2.92 (dd, J=12.8, 6.4 Hz, 1H), 2.96 (dd, J=12.8, 6.4 Hz, 1H), 4.46 (dd, J=12.4, 6.4 Hz, 1H), 4.95 (m, 2H), 5.05 (d, J=8.8 Hz, 1H, NH), 6.65 (d, J=8.0 Hz, 1H), 6.66 (s, 1H), 6.73 (d, J=8.0 Hz, 1H). MS (ESI) m/z 434.1 (M+Na)+ and 410.1 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-1f5f2081a849482284008a0588957a1b
Source dataset
uspto-grants-2010_05
Patent number
US07709527B2

Reaction notes

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