(S)-2-((2R,3R)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((2S,3S)-2-hydroxypentan-3-yl)-2-methylpent-4-enamide → (1R,2R,4S)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-4-((4S,5S)-4-ethyl-5-methyl-4,5-dihydrooxazol-2-yl)-4-methylhept-6-en-1-ol

HRID 932105Notes

Reaction equation

HRID 932105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[OH:25])[CH2:9][C@:10]([CH3:23])([CH2:20][CH:21]=[CH2:22])[C:11]([NH:13][C@@H:14]([CH2:18][CH3:19])[C@@H:15]([OH:17])[CH3:16])=O)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:9][C@:10]([C:11]2[O:17][C@@H:15]([CH3:16])[C@H:14]([CH2:18][CH3:19])[N:13]=2)([CH3:23])[CH2:20][CH:21]=[CH2:22])[C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[OH:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 66552261(S)-2-((2R,3R)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((2S,3S)-2-hydroxypentan-3-yl)-2-methylpent-4-enamide

Product 1

HCID 66552262(1R,2R,4S)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-4-((4S,5S)-4-ethyl-5-methyl-4,5-dihydrooxazol-2-yl)-4-methylhept-6-en-1-ol

Reagents, catalysts & solvents 3

HCID 61578Diammonium molybdateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-((2R,3R)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((2S,3S)-2-hydroxypentan-3-yl)-2-methylpent-4-enamide (127 mg, 0.265 mmol) in toluene (5309 μl) was added ammonium molybdate ((NH4)2MoO4) (5.20 mg, 0.027 mmol) and heated to reflux under Dean-Stark conditions overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with sat. NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated. Purification by column chromatography using 20 to 40% ethyl acetate in hexanes afforded (1R,2R,4S)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-4-((4S,5S)-4-ethyl-5-methyl-4,5-dihydrooxazol-2-yl)-4-methylhept-6-en-1-ol

Workup

  1. temperatureheated
  2. temperatureto reflux under Dean-Stark conditions overnight
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-0139e76eed6b42e28ff30bf762c7194b
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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