HCID 68713472, compound → HCID 59201461, compound

HRID 451897Notes

Reaction equation

HRID 451897 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:19][C:20]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([C@H:28]([C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[C:38]=3[OH:45])[O:29][CH2:30][CH2:31][NH:32][C:33](=[O:36])[O:34][CH3:35])[CH2:23]2)=[O:21])[CH2:9][N:10](C)[C:11](OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:7][C@H:8]([NH:19][C:20]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([C@H:28]([C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[C:38]=3[OH:45])[O:29][CH2:30][CH2:31][NH:32][C:33](=[O:36])[O:34][CH3:35])[CH2:23]2)=[O:21])[CH2:9][NH:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 68713472HCID 68713472, compound

Product 1

HCID 59201461HCID 59201461, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

methyl 2-((R)—((R)-1-((S)-1-cyclohexyl-3-(N-methyl-N-(tert-butoxycarbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)(3,5-difluoro-2-hydroxyphenyl)methoxy)ethylcarbamate (100 mg, 0.131 mmol) was dissolved in MeOH (1 mL) and Pd/C (20 mg) was added to it. The reaction mixture was stirred in 30 psi at room temperature for 2 h. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC to afford methyl 2-((R)—((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)(3,5-difluoro-2-hydroxyphenyl)methoxy)ethylcarbamate (20 mg, 28%).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8de695f088bd4b878103f67b5fcbd3a6
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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