(S)-3-((R,Z)-6-(Benzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one → (S)-3-((R)-2-(4-Fluoro-3-methylphenoxy)-6-hydroxyhexanoyl)-4-isopropyloxazolidin-2-one

HRID 1361056Notes

Reaction equation

HRID 1361056 reaction equation
C([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@@H:13]([O:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([CH3:33])[CH:27]=1)[C:14]([N:16]1[C@@H:20]([CH:21]([CH3:23])[CH3:22])[CH2:19][O:18][C:17]1=[O:24])=[O:15])C1C=CC=CC=1>[Pd].CCO>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C@H:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:14]([N:16]2[C@@H:20]([CH:21]([CH3:23])[CH3:22])[CH2:19][O:18][C:17]2=[O:24])=[O:15])=[CH:27][C:28]=1[CH3:33]

Participants

4

Reactant 1

HCID 59775160(S)-3-((R,Z)-6-(Benzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one

Product 1

HCID 59775192(S)-3-((R)-2-(4-Fluoro-3-methylphenoxy)-6-hydroxyhexanoyl)-4-isopropyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-3-((R,Z)-6-(benzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one (250 mg, 0.54 mmol) was dissolved into 5 mL EtOH and to it added 10% Pd/C (250 mg). The solution was saturated with H2 (stream of H2 bubbled through solution) and then stirred for 3 h at room temperature under an atmosphere of hydrogen balloon. The mixture was filtered through a bed of Celite and rinsed with ethyl acetate. The solvent was removed under reduced pressure and the crude product used directly in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. washrinsed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product used directly in the next step without further purification

Sources & evidence

ORD record
ord-a814c730b07149d1a7d2be346d834683
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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