Benzyl (S)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoate → (S)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid

HRID 58805Notes

Reaction equation

HRID 58805 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH:21][C:22](=[O:35])[C@@H:23]([NH:25][C:26](=[O:34])[CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH3:24])[C:11]([O:13]CC2C=CC=CC=2)=[O:12])=[CH:5][CH:4]=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C@H:10]([NH:21][C:22](=[O:35])[C@@H:23]([NH:25][C:26](=[O:34])[CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH3:24])[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 117870627Benzyl (S)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoate

Product 1

HCID 68247340(S)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-benzyl 3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoate (5.00 g, 10.4 mmol) and Pd/C (10%, 1.0 g) in THF (50 mL) was stirred under a hydrogen atmosphere for 2 h. The mixture was filtered and concentrated to afford (S)-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid (3.3 g, 94% yield) as a colorless solid. 1H NMR (300 MHz, DMSO-d6): δ 8.24 (d, J=8.1 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.13 (m, 2H), 6.82 (m, 2H), 4.35 (m, 2H), 3.71 (s, 3H), 3.63-3.56 (m, 4H), 2.99-2.65 (m, 4H), 2.41-2.38 (m, 4H), 1.20 (d, J=6.9 Hz, 3H). MS (EI) for C19H27N3O6, found 394.5 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a2e3b3b7606644429a4cf49de66eb5f6
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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