HCID 59176533, compound → HCID 59176420, compound

HRID 628691Notes

Reaction equation

HRID 628691 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:24]C(=O)OCC1C=CC=CC=1)[C:14](=[O:23])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:24][C@H:13]([C:14](=[O:23])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59176533HCID 59176533, compound

Product 1

HCID 59176420HCID 59176420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-benzyl 6-((tert-butoxycarbonyl)-amino)-1-oxo-1-(pyridin-2-ylmethylamino)hexan-2-ylcarbamate, 27, (3.8 g, 8.2 mmol) in methanol (80 mL) was added palladium (10 wt % on carbon, 0.5 g). The mixture was stirred under a hydrogen atmosphere for 2 h. The mixture was filtered through Celite and washed with methanol. The resulting filtrate was concentrated in vacuo. The crude residue was used without further purification: ESI+ MS: m/z (rel intensity) 337.2 (100, [M+H]+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with methanol
  3. concentrationThe resulting filtrate was concentrated in vacuo
  4. customThe crude residue was used without further purification

Sources & evidence

ORD record
ord-44c0083b8f5b4fa8b614ea67d079176c
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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