Acetic Acid → HCID 136508367, compound

HRID 1034972Notes

Reaction equation

HRID 1034972 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:9]2[NH:10][C:11](=[O:18])[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[C:8]=2[C:7]([C@H:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[N:6]1)#N.C(O)(=[O:36])C>[Ni]>[O:18]=[C:11]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=2[C:8]2[C:7]([C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])=[N:6][N:5]([CH2:4][CH2:3][CH:1]=[O:36])[C:9]=2[NH:10]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136492069HCID 136492069, compound

Product 1

HCID 136508367HCID 136508367, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of Example 72A (2.0 g, 4.5 mmol) in acetic acid (10 ml) was treated with Raney nickel (200 mg) at rt. The reaction mixture was stirred under hydrogen for 6 h. Solid material was filtered off and the filtrate was concentrated. The residue was separated by flash chromatography to give Example 77A. Yield: 0.5 g (25%). MS (DCI): m/z 449 (M+H)+.

Workup

  1. filtrationSolid material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was separated by flash chromatography
  4. customto give Example 77A

Sources & evidence

ORD record
ord-74ccf5df26614c76bb71910ab868ed08
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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