HCID 117608222, compound → (R)-2-((1R,3S)-3-hydroxycyclopentanecarboxamido)propanoic acid

HRID 58876Notes

Reaction equation

HRID 58876 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([NH:9][C@H:10]([CH3:21])[C:11]([O:13]CC2C=CC=CC=2)=[O:12])=[O:8])[CH2:3]1>CO.[Pd]>[OH:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([NH:9][C@H:10]([CH3:21])[C:11]([OH:13])=[O:12])=[O:8])[CH2:3]1

Participants

4

Reactant 1

HCID 117608222HCID 117608222, compound

Product 1

HCID 117690994(R)-2-((1R,3S)-3-hydroxycyclopentanecarboxamido)propanoic acidYield 131.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 1 g) was added to a solution of compound (R)-benzyl 2-((1R,3S)-3-hydroxycyclopentanecarboxamido)propanoate (500 mg, 1.7 mmol) in MeOH (20 mL). The suspension was stirred under hydrogen atmosphere at ambient temperature for 2 h. Pd/C was filtered off and washed with MeOH (5 mL). The filtrate and washings were combined and concentrated to dryness to afford (R)-2-((1R,3S)-3-hydroxycyclopentanecarboxamido)propanoic acid (450 mg, quantitative). (R)-2-((1S,3R)-3-hydroxycyclopentanecarboxamido)propanoic acid was obtained in a similar manner.

Workup

  1. filtrationPd/C was filtered off
  2. washwashed with MeOH (5 mL)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-742f2277ae264ed1b8deda179f7d20d5
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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