HCID 20134255, compound → HCID 20134248, compound

HRID 1633093Notes

Reaction equation

HRID 1633093 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[C:20]([CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:19]=2)[OH:17])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]>C(O)C.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:19]=2)[OH:17])[CH3:13])=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 20134255HCID 20134255, compound

Product 1

HCID 20134248HCID 20134248, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(4-benzyloxy-3-methylsulphonylmethylphenyl)-2-hydroxyethanamine(2.3 g) was converted to the hydrochloride salt and hydrogenated in ethanol (200 ml) in a Parr hydrogenerator at 50 psi and 25° for 2 hours in the presence of 10% palladium on charcoal (0.5 g). The catalyst was removed and the product was isolated as a mixture of diastereoisomers, mp 145°-148° (methanol:ether). τ(d6DMSO) 8.90 (3H, d, J=6 Hz), 7.2 (3H, s), 6.20-7.10 (6H, m), 6.20 (3H, s), 5.70 (2H, s), 5.00 (1H, m), 390 (1H, b), 2.40-3.10 (5H, m), 2.08 (2H, d, J=8 Hz)., 0.70 (1H, br),-0.10 (1H, br).

Workup

  1. customThe catalyst was removed
  2. customthe product was isolated as a mixture of diastereoisomers, mp 145°-148° (methanol:ether)

Sources & evidence

ORD record
ord-972754568be04ce1930cd83c672b3344
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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