HCID 59840877, compound → HCID 16112852, compound

HRID 1875716Notes

Reaction equation

HRID 1875716 reaction equation
C([O:8][N:9]([CH2:12][C@@H:13]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH:10]=[O:11])C1C=CC=CC=1.[H][H]>[Pd]>[OH:8][N:9]([CH2:12][C@@H:13]([C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH2:24][CH2:25]1)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 59840877HCID 59840877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16112852HCID 16112852, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of N-(benzyloxy)-N-((2S)-2-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-4-methylpentyl)formamide (100 mg, 0.22 mmol) was hydrogenated under 1 atm of hydrogen in the presence of Pd/C (10%, 23 mg, 0.02 mmol, 0.1 eq.) for 2 h at room temperature. The mixture was filtered on a bed of cellite, evaporated to give the title product as an orange foam (60 mg, 75%). HPLC, Rt: 1.95 min (purity: 100%). M+ (LC-MS (ESI)): 364.4.

Workup

  1. filtrationThe mixture was filtered on a bed of cellite
  2. customevaporated

Sources & evidence

ORD record
ord-9f06ea3318e747dab60fc95653f32b3b
Source dataset
uspto-grants-2012_11
Patent number
US08309579B2

Reaction notes

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