HCID 130394592, compound → HCID 117607802, compound

HRID 58807Notes

Reaction equation

HRID 58807 reaction equation
[OH:1][C@H:2]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C@H:3]([NH:14][C:15](=[O:28])[C@@H:16]([NH:18][C:19](=[O:27])[CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[CH3:17])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>C1COCC1.[Pd]>[OH:1][C@H:2]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[C@H:3]([NH:14][C:15](=[O:28])[C@@H:16]([NH:18][C:19](=[O:27])[CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[CH3:17])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 130394592HCID 130394592, compound

Product 1

HCID 117607802HCID 117607802, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R)-benzyl 3-hydroxy-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholino acetamido)propanamido)propanoate (2.0 g, 4.0 mmol) in THF (40 mL) was added Pd/C (500 mg, 10%). The mixture was stirred under a hydrogen atmosphere (1 atm) at ambient temperature overnight and then filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue was washed with EtOAc (10 mL) to afford (2S,3R)-3-hydroxy-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid (1.30 g, 78% yield) as a colorless solid.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. washthe residue was washed with EtOAc (10 mL)

Sources & evidence

ORD record
ord-f425c6a51d364bb0967b957e504c943b
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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