HCID 131737020, compound → (2S,3R)-3-hydroxy-2-((S)-3-hydroxy-2-(2-morpholinoacetamido)propanamido)-3-(4-methoxyphenyl)propanoic acid

HRID 58812Notes

Reaction equation

HRID 58812 reaction equation
[OH:1][C@H:2]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C@H:3]([NH:14][C:15](=[O:29])[C@@H:16]([NH:19][C:20](=[O:28])[CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[CH2:17][OH:18])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>C1COCC1.[Pd]>[OH:1][C@H:2]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[C@H:3]([NH:14][C:15](=[O:29])[C@@H:16]([NH:19][C:20](=[O:28])[CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[CH2:17][OH:18])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 131737020HCID 131737020, compound

Product 1

HCID 117608085(2S,3R)-3-hydroxy-2-((S)-3-hydroxy-2-(2-morpholinoacetamido)propanamido)-3-(4-methoxyphenyl)propanoic acidYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R)-benzyl 3-hydroxy-2-((S)-3-hydroxy-2-(2-morpholinoacetamido)propanamido)-3-(4-methoxyphenyl)propanoate (349 mg, 0.680 mmol) in THF (20 mL) was added Pd/C (100 mg, 10%). The mixture was stirred under a hydrogen atmosphere (1 atm) at ambient temperature overnight then filtered through a pad of celite. The filtrate was concentrated to afford (2S,3R)-3-hydroxy-2-((S)-3-hydroxy-2-(2-morpholinoacetamido)propanamido)-3-(4-methoxyphenyl)propanoic acid (121 mg, 42% yield) as a colorless solid.

Workup

  1. filtrationthen filtered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c5d6a988b36c4a77a0bd2a58231390d3
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…