Acetic Acid → HCID 67222030, compound

HRID 876587Notes

Reaction equation

HRID 876587 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][C@H:13]([C@@H:17]([OH:32])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[N:29]O)[NH2:28])=[CH:23][C:22]=3[Cl:31])=[O:19])[C:12]2=[O:33])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]([OH:37])=[O:36]>CCO.[Ni]>[C:35]([OH:37])(=[O:36])[CH3:34].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18](=[O:19])[C@@H:17]([C@H:13]2[O:14][CH2:15][CH2:16][N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=3)[C:12]2=[O:33])[OH:32])=[C:22]([Cl:31])[CH:23]=1)(=[NH:28])[NH2:29]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86653953HCID 86653953, compound

Product 1

HCID 67222030HCID 67222030, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 66-2 (19 mg) in EtOH (3 mL), were added cat. Raney-Ni and AcOH (0.1 mL). The mixture was stirred under hydrogen atmosphere for 3 hours at room temperature. The mixture was filtered with Celite® pad to remove catalyst. The filtrate was concentrated with toluene in vacuo. The residue was dried by vacuum pump to obtain EXAMPLE 66 (15 mg) as a colorless amorphous solid.

Workup

  1. filtrationThe mixture was filtered with Celite® pad
  2. customto remove catalyst
  3. concentrationThe filtrate was concentrated with toluene in vacuo
  4. customThe residue was dried by vacuum pump

Sources & evidence

ORD record
ord-09de37ed1e3745f7bc6e8a241bfc687f
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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