HCID 67350536, compound → HCID 67349808, compound

HRID 1916341Notes

Reaction equation

HRID 1916341 reaction equation
[F:1][C:2]1[C:11]2[CH:12]([CH2:14][NH:15][CH2:16][CH2:17][C@H:18]3[O:22][C:21](=[O:23])[N:20]([C:24]4[CH:25]=[CH:26][C:27]5[O:32][CH2:31][C:30](=[O:33])[NH:29][C:28]=5[CH:34]=4)[CH2:19]3)[CH2:13][N:9]3[C:10]=2[C:5]([CH:6]=[CH:7][C:8]3=[O:35])=[CH:4][CH:3]=1>CO.CC(O)=O.[Pd]>[F:1][C:2]1[C:11]2[CH:12]([CH2:14][NH:15][CH2:16][CH2:17][C@@H:18]3[O:22][C:21](=[O:23])[N:20]([C:24]4[CH:25]=[CH:26][C:27]5[O:32][CH2:31][C:30](=[O:33])[NH:29][C:28]=5[CH:34]=4)[CH2:19]3)[CH2:13][N:9]3[C:10]=2[C:5]([CH2:6][CH2:7][C:8]3=[O:35])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67350536HCID 67350536, compound

Product 1

HCID 67349808HCID 67349808, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of the compound of Example 2 (60 mg) in MeOH/AcOH (1:1, 2 mL) was hydrogenated over Pd/C (133 mg) overnight. The catalyst was filtered off and thoroughly washed with MeOH and MeOH/DCM. The filtrate was concentrated under reduced pressure. The residue was taken up in water and 28% aq. NH4OH, filtered, washed with water and TBME and dried under reduced pressure, affording an off-white foam (45 mg; 75% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. washthoroughly washed with MeOH and MeOH/DCM
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtration28% aq. NH4OH, filtered
  5. washwashed with water and TBME
  6. customdried under reduced pressure
  7. customaffording an off-white foam (45 mg; 75% yield)

Sources & evidence

ORD record
ord-afb131a9fdf74516aa22fe5c4ec0607c
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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