(2S,3S,5S)-5-amino-2-(dibenzylamino)-1-phenyl-6-(4-pyridin-2-ylphenyl)hexan-3-ol → (2S,3S,5S)-2,5-diamino-1-phenyl-6-(4-pyridin-2-ylphenyl)hexan-3-ol
Reaction equation
[NH2:1][C@@H:2]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:32][CH:31]=1)[CH2:3][C@H:4]([OH:28])[C@@H:5]([N:13](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[NH2:13][C@H:5]([C@@H:4]([OH:28])[CH2:3][C@@H:2]([NH2:1])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:34][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
A solution of the product of Example 2-2 (3.8 g) in methanol (65 mL) in a three-necked round bottom flask equipped with a condenser was flushed with nitrogen, treated with water (5 mL), ammonium formate (2.5 g) and Pd/C (1.0 g), and stirred under nitrogen at 60° C. for 12 hours. The reaction mixture was cooled, filtered, and concentrated. A solution of the residue in dichloromethane (100 mL) was washed with saturated aqueous NaHCO3 (3×50 mL). The isolated dichlormethane layer was concentrated to afford 3.3 g of the crude product.
Workup
- customwas flushed with nitrogen
- additiontreated with water (5 mL), ammonium formate (2.5 g) and Pd/C (1.0 g)
- temperatureThe reaction mixture was cooled
- filtrationfiltered
- concentrationconcentrated
- washA solution of the residue in dichloromethane (100 mL) was washed with saturated aqueous NaHCO3 (3×50 mL)
- concentrationThe isolated dichlormethane layer was concentrated
Sources & evidence
- ORD record
- ord-5d2290c8838945c0b296c1e963f73d85
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834043B2
Reaction notes
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