HCID 66750799, compound → HCID 66750594, compound

HRID 504153Notes

Reaction equation

HRID 504153 reaction equation
C([O:8][C:9](=[O:42])[C@@H:10]([NH:23][C:24]([C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)(=[O:34])=[O:33])=[O:25])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][F:22])=[CH:14][CH:13]=1)C1C=CC=CC=1>[Pd].C(O)C>[F:41][C:37]1[CH:36]=[C:35]([S:32]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C@H:26]2[C:24]([NH:23][C@@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][F:22])=[CH:14][CH:13]=2)[C:9]([OH:42])=[O:8])=[O:25])(=[O:34])=[O:33])[CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 1

HCID 66750799HCID 66750799, compound2×

Product 1

HCID 66750594HCID 66750594, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of (S)-2-{[(S)-1-(3-fluoro-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-[4-(3-fluoro-propoxy)-phenyl]-propionic acid benzyl ester (1.9 g, 3.1 mmol) (compound 18a), ethanol (50 mL), and 10% Pd on carbon was hydrogenated at 30 psi for 3 h. The suspension was filtered through Celite®, washed with dichloromethane and the filtrate concentrated. The resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel to provide 1.04 g (64.7%) of the title compound as a white powder.

Workup

  1. filtrationThe suspension was filtered through Celite®
  2. washwashed with dichloromethane
  3. concentrationthe filtrate concentrated
  4. customThe resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel

Sources & evidence

ORD record
ord-44a83699756340bd93b00ba76a6aff45
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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