HCID 131736820, compound → HCID 118292845, compound

HRID 1486844Notes

Reaction equation

HRID 1486844 reaction equation
C([O:8][C:9](=[O:44])[CH2:10][C@:11]1([C:34]([O:36]CC2C=CC=CC=2)=[O:35])[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23](=[O:33])[C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[CH:17]=2)[CH2:12]1)C1C=CC=CC=1>[Pd].C1COCC1>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]([O:22][C:18]2[CH:17]=[C:16]([C:13]3[CH2:12][C@@:11]([CH2:10][C:9]([OH:44])=[O:8])([C:34]([OH:36])=[O:35])[O:15][N:14]=3)[CH:21]=[CH:20][CH:19]=2)=[O:33])=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 131736820HCID 131736820, compound

Product 1

HCID 118292845HCID 118292845, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl (5R)-5-(2-(benzyloxy)-2-oxoethyl)-3-(3-((4-nitrobenzoyl)oxy)phenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (77.5 g), 10% Pd/C (containing about 55% water, 7.8 g), and THF (780 mL) was stirred at room temperature for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure to obtain (5R)-3-(3-((4-aminobenzoyl)oxy)phenyl)-5-(carboxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid as a crude product.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c7ba758750a94962b815f08096293a19
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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