HCID 69818442, compound → HCID 69819735, compound

HRID 1006360Notes

Reaction equation

HRID 1006360 reaction equation
[CH3:1][O:2][C:3](=[O:43])[C@H:4]([NH:32]C(OCC1C=CC=CC=1)=O)[CH2:5][N:6]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[CH2:7][C:8](=O)[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1.C(N(CC)CC)C.[Pd]>[CH3:1][O:2][C:3]([C@H:4]1[CH2:5][N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])[CH2:7][CH:8]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:32]1)=[O:43]

Participants

5

Reactant 1

HCID 69818442HCID 69818442, compound

Product 1

HCID 69819735HCID 69819735, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

(2R)-2-Benzyloxycarbonylamino-3-[N-(2-methoxybenzyl)-N-(2-oxo-3,3-diphenylpropyl)amino]propionic acid methyl ester (1.55 g) was dissolved in a mixture of tetrahydrofuran (50 ml) and triethylamine (0.744 ml), and the whole was hydrogenated over 10% palladium-charcoal (50% wet, 0.15 g) at room temperature under atmospheric pressure for 4 hours. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2R)-6-benzhydryl-4-(2-methoxybenzyl)piperazine-2-carboxylic acid methyl ester (663.8 mg) as a yellow oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0c0c6e08c93f4f539e86f7483607f279
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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