(2S)-3-cyclohexyl-1-(morpholin-4-yl)-1-oxopropan-2-yl N-[(2R)-1-(benzyloxy)-3-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-2-yl]carbamate → HCID 23648372, compound

HRID 15273Notes

Reaction equation

HRID 15273 reaction equation
[CH:1]1([CH2:7][C@H:8]([O:17][C:18](=[O:41])[NH:19][C@@H:20]([CH2:32][O:33]CC2C=CC=CC=2)[CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=3)[CH2:24][CH2:23]2)[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:7][C@H:8]([O:17][C:18](=[O:41])[NH:19][C@@H:20]([CH2:32][OH:33])[CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=3)[CH2:24][CH2:23]2)[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 11421700(2S)-3-cyclohexyl-1-(morpholin-4-yl)-1-oxopropan-2-yl N-[(2R)-1-(benzyloxy)-3-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-2-yl]carbamate

Product 1

HCID 23648372HCID 23648372, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound of Example 10 (50 mg, 0.088 mmol) was dissolved in a minimum amount of methanol (approx. 1-2 mL) and a catalytic amount of 10% Pd/C was added. Air was purged from the reaction vessel and H2 gas was introduced via a balloon. The reaction mixture was stirred for several hours under a H2 atmosphere, after which point the starting material had disappeared by LCMS. The Pd/C was filtered and the crude material was purified by reverse-phase HPLC to afford the title compound (30 mg, 71% yield).

Workup

  1. customAir was purged from the reaction vessel and H2 gas
  2. additionwas introduced via a balloon
  3. filtrationThe Pd/C was filtered
  4. customthe crude material was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-1c828bccb3f64cab96daff055e1f490d
Source dataset
uspto-grants-2010_06
Patent number
US07732449B2

Reaction notes

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