HCID 69883297, compound → HCID 69883181, compound

HRID 843399Notes

Reaction equation

HRID 843399 reaction equation
[CH3:1][N:2]([C@H:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])[C:3](=[O:27])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19]CC2C=CC=CC=2)=[CH:15][CH:14]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>CO.[Pd]>[CH3:1][N:2]([C@H:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])[C:3](=[O:27])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 69883297HCID 69883297, compound

Product 1

HCID 69883181HCID 69883181, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 2-[N-methyl-N-((R/S)-α-t-butoxycarbonylmethyl-4-benzyloxyphenylacetyl)amino]-(R)-propionate 48c (3.0 g, 6.59 mmol) in MeOH (75 mL) was hydrogenated under atmospheric pressure using 10% Pd/C (0.6 g) as a catalyst for a period of 4.5 hours. The catalyst was filtered off and the solvent was removed under reduced pressure. The residue was purified on a silica gel column using 40% EtOAc/hexane as an eluent to afford the phenol product (1.5 g, 62%) as a solid. MS (CI—NH3): (M+H)+=366.

Workup

  1. customof 4.5 hours
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-d1248c4a9d5e4515a09c49191dc6df39
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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