(2S)-2-Amino-3,3-dimethyl-1-butanol → (S)-2-((2R,3R)-2-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-2-methylpent-4-enamide

HRID 932241

Reaction equation

HRID 932241 reaction equation
[NH2:1][C@H:2]([CH2:7][OH:8])[C:3]([CH3:6])([CH3:5])[CH3:4].[CH2:9]([C@@:12]1([CH3:33])[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C@H:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[O:14][C:13]1=[O:32])[CH:10]=[CH2:11]>C(OCC)(=O)C>[Cl:24][C:20]1[CH:19]=[C:18]([C@H:16]([C@H:15]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[OH:14])[CH2:17][C@:12]([CH3:33])([CH2:9][CH:10]=[CH2:11])[C:13]([NH:1][C@@H:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH2:7][OH:8])=[O:32])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2734079(2S)-2-Amino-3,3-dimethyl-1-butanolHCID 58573721(3S,5R,6R)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyltetrahydro-2H-pyran-2-one

Product 1

HCID 67999110(S)-2-((2R,3R)-2-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-2-methylpent-4-enamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(S)-tert-leucinol (0.937 g, 7.99 mmol) and (3S,5R,6R)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyltetrahydro-2H-pyran-2-one (1 g, 2.66 mmol; Example 261, Step F) were combined in a reaction flask and heated to 100° C. After 2d, the reaction mixture was cooled to RT and dissolved in ethyl acetate. The organic phase was washed with 3×10 mL 1N HCl and 1×10 mL brine, dried over MgSO4, filtered and concentrated to afford the title compound.

Workup

  1. washThe organic phase was washed with 3×10 mL 1N HCl and 1×10 mL brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e29e31727b24172b09720d3196e79cc
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Linked notes

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