1-Phenethylamine, (+)- → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamide

HRID 1700969Notes

Reaction equation

HRID 1700969 reaction equation
[C:1]([C@@H:4]([NH:9][C:10](=[O:41])[C@@H:11]([C@H:33]1[C:37](=[O:38])[O:36][C:35]([CH3:40])([CH3:39])[O:34]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)=[CH:20][CH:19]=1)[C:5]([CH3:8])([CH3:7])[CH3:6])(O)=[O:2].[C:42]1([C@H:48]([NH2:50])[CH3:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(OCC)(=O)C>[CH3:39][C:35]1([CH3:40])[O:34][C@@H:33]([C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)=[CH:20][CH:19]=2)[C:10]([NH:9][C@H:4]([C:1]([NH:50][C@@H:48]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH3:49])=[O:2])[C:5]([CH3:6])([CH3:7])[CH3:8])=[O:41])[C:37](=[O:38])[O:36]1

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 131723127(2R)-N-[(1S)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamide

Product 1

HCID 131723126(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-[(3'-methoxy-2-methylbiphen-4-yl)propyl]pentanamideYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to the method of Example 25(a), (2R)-N-[(1S)-1-(carboxy)-2,2-dimethylpropyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pentanamide (Preparation 34)(150 mg, 0.28 mmol) was reacted with (R)-1-phenylethylamine (35 μl , 0.28 mmol) at room temperature for 2.5 h. The mixture was poured into ethyl acetate (75 mL) and washed with 0.5M aqueous sodium dihydrogenphosphate (2×50 mL) and 5% aqueous sodium bicarbonate (50 mL) (solid sodium chloride was added to give phase separation). The organic solution was dried (Na2SO4) and concentrated under reduced pressure. The residual oil was purified by flash chromatography (eluting with hexane:ethyl acetate=35:65) to give (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-N-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-5-[(3′-methoxy-2-methylbiphen-4-yl)propyl]pentanamide as a white solid (133 mg, 76%).

Workup

  1. washwashed with 0.5M aqueous sodium dihydrogenphosphate (2×50 mL) and 5% aqueous sodium bicarbonate (50 mL) (solid sodium chloride was added to give phase separation)
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residual oil was purified by flash chromatography (eluting with hexane:ethyl acetate=35:65)

Sources & evidence

ORD record
ord-61a76b82227f4af6b3b22e34b624cde7
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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