Tetrahydrofuran → HCID 118292840, compound

HRID 1486842Notes

Reaction equation

HRID 1486842 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH2:19][C@@:18]([CH2:23][C:24]([OH:26])=[O:25])([C:20]([OH:22])=[O:21])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C1COCC1>[Pd].CO>[C:24]([CH2:23][C@:18]1([C:20]([OH:22])=[O:21])[O:17][N:16]=[C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[CH2:19]1)([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 118292824HCID 118292824, compound

Product 1

HCID 118292840HCID 118292840, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (5R)-3-(3-(benzyloxy)phenyl)-5-(carboxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid (75.0 g), 10% Pd/C (containing about 55% water, 7.5 g), and THF (750 mL) was stirred at room temperature for 15 hours under a hydrogen atmosphere. To the reaction mixture, methanol (150 mL) was added, then the catalyst was filtered and washed with methanol (375 mL). The filtrate was concentrated under reduced pressure to obtain (5R)-5-(carboxymethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid as a crude product.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with methanol (375 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df6d374ede4a4568b50f750bc6ae9c00
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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