(S)-benzyl 2-(2-morpholinoacetamido)propanoate → (2-morpholinoacetyl)-L-alanine

HRID 58887Notes

Reaction equation

HRID 58887 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([NH:10][C@@H:11]([CH3:22])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[O:9])[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([NH:10][C@@H:11]([CH3:22])[C:12]([OH:14])=[O:13])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 117607729(S)-benzyl 2-(2-morpholinoacetamido)propanoate

Product 1

HCID 117607686(2-morpholinoacetyl)-L-alanineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To Pd/C (10%, 5.0 g) was added a solution of (S)-benzyl 2-(2-morpholinoacetamido)propanoate (20.0 g, 69.0 mmol) in MeOH (200 mL). The mixture was stirred under a hydrogen atmosphere at ambient temperature for 4 h, then it was filtered and rinsed with MeOH (200 mL). The filtrate and washings were combined and concentrated to dryness to afford crude product which was washed with EtOAc (2×100 mL) and dried under vacuum to afford (S)-2-(2-morpholinoacetamido)propanoic acid (12.8 g, 86% yield) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 7.95 (m, 1H), 4.25 (m, 1H), 3.70 (m, 4H), 3.08 (d, J=15.4 Hz, 2H), 2.40-2.55 (m, 4H), 1.30 (d, J=6.6 Hz, 3H).

Workup

  1. filtrationit was filtered
  2. washrinsed with MeOH (200 mL)
  3. concentrationconcentrated to dryness
  4. customto afford crude product which
  5. washwas washed with EtOAc (2×100 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6f09ed9c10a2471fa00381330159a0d9
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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