HCID 67154141, compound → HCID 58280571, compound

HRID 331676Notes

Reaction equation

HRID 331676 reaction equation
C([O:8][C:9](=[O:33])[C@@H:10]([O:25][C@H:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:14][CH:13]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[Cl:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][C@H:10]([O:25][C@H:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:27])[C:9]([OH:33])=[O:8])=[CH:17][CH:16]=2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 67154141HCID 67154141, compound

Product 1

HCID 58280571HCID 58280571, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-3-(3′-chloro-biphenyl-4-yl)-2-((S)-1-ethoxycarbonyl-ethoxy)-propionic acid benzyl ester and 10% Pd/C wet in EtOAc was hydrogenated under H2 balloon for 30 mins. The reaction was filtered off the catalyst and concentrated. The residue was purified by HPLC (15 to 70% ACN—H2O (0.1% TFA)) to give oil: 128 mg. HPLC retention time=1.07 minutes (condition C); MS (m−1)=375.

Workup

  1. customfor 30 mins
  2. filtrationThe reaction was filtered off the catalyst
  3. concentrationconcentrated
  4. customThe residue was purified by HPLC (15 to 70% ACN—H2O (0.1% TFA))
  5. customto give oil

Sources & evidence

ORD record
ord-158e00eb2c044ae1a0201d53ae8d53ec
Source dataset
uspto-grants-2014_11
Patent number
US08877786B2

Reaction notes

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