(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 1048419Notes

Reaction equation

HRID 1048419 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-d03d5ae224ff42f8880e37b60b3c8f86
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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