Triethylamine → HCID 54057429, compound

HRID 465641Notes

Reaction equation

HRID 465641 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].C(N(CC)CC)C.[C:40]([CH2:44][C:45](Cl)=[O:46])([CH3:43])([CH3:42])[CH3:41]>C1COCC1.C(OCC)(=O)C>[CH3:17][CH:15]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:6]=1[NH:5][C:3](=[O:4])[C@@H:2]([NH:1][C:45](=[O:46])[CH2:44][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:20]=1)[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 54099304HCID 54099304, compound

Product 1

HCID 54057429HCID 54057429, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a cooled (0° C.) solution of (S)-α-amino-N-[2,6-bis(1-Methylethyl)phenyl]-4-(phenylmethoxy)benzenepropanamide (1.15 g, 2.67 mmol) and triethylamine (0.37 mL, 2.67 mmol) in THF (50 mL) was added tert-butylacetylchloride (0.39 mL, 2.80 mmol) dropwise. The resulting slurry was warmed to 25° C. and stirred (1 hour, 25° C.). The resulting slurry was diluted with ethyl acetate (200 mL). The organic layer was washed with 1.0N aqueous HCl (1×65 mL), with brine (1×65 mL), with saturated aqueous sodium bicarbonate (1×65 mL), with brine again (1×65 mL), then dried (MgSO4) and concentrated. The resulting oil was triturated with ether, and cooled. The resulting solid was collected by filtration, washed with cold ether, and dried in a vacuum oven at 40° C. to yield 1.2 g (85.1%) of the title compound as a white solid, melting point 209°-211.5° C.

Workup

  1. washThe organic layer was washed with 1.0N aqueous HCl (1×65 mL), with brine (1×65 mL), with saturated aqueous sodium bicarbonate (1×65 mL), with brine again (1×65 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting oil was triturated with ether
  5. temperaturecooled
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with cold ether
  8. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-557b346da1be4c5582bb57dc49d6cd8e
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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