Triphenylphosphine → (S)-4-Benzyl-3-[(2S)-3-(4-{2-[2-(4-chloro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-methyl-phenyl)-2-ethoxy-propionyl]-oxazolidin-2-one

HRID 1394694Notes

Reaction equation

HRID 1394694 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[C@@H:15]([O:25][CH2:26][CH3:27])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[O:37][C:38]([CH3:44])=[C:39]([CH2:41][CH2:42]O)[N:40]=2)=[CH:32][CH:31]=1.O=C(CC)CC(OC)=O.ClC1C=CC(C(N)=O)=CC=1.CC1OC(C2C=CC=CC=2)=NC=1CCO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[C@@H:15]([O:25][CH2:26][CH3:27])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:42][CH2:41][C:39]2[N:40]=[C:36]([C:33]3[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=3)[O:37][C:38]=2[CH3:44])=[CH:19][C:18]=1[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 7

HCID 11776TriphenylphosphineHCID 120844-ChlorobenzamideHCID 121699Methyl 3-oxovalerateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 222739062-[2-(4-Chloro-phenyl)-5-methyl-oxazol-4-yl]-ethanolHCID 68615907(S)-4-Benzyl-3-[(2S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionyl]-oxazolidin-2-one

Product 1

HCID 69282429(S)-4-Benzyl-3-[(2S)-3-(4-{2-[2-(4-chloro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-methyl-phenyl)-2-ethoxy-propionyl]-oxazolidin-2-oneYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a ice cold solution of (S)-4-benzyl-3-[(2S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionyl]-oxazolidin-2-one (100 mg, 260 μmol), 2-[2-(4-chloro-phenyl)-5-methyl-oxazol-4-yl]-ethanol (93 mg, 390 μmol) (prepared from methyl 3-oxopentanoate and 4-chloro-benzamide in analogy to the sequence described for the synthesis of 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethanol in M. Scalone, PCT WO 01/79202 A1) and triphenylphosphine (103 mg, 390 mmol) in tetrahydrofuran (2.5 ml) was added diethyl azodicarboxylate (61 μl, 390 μmol). The cooling bath was removed and stirring was continued for 12 h. Evaporation of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 70 mg (120 μmol, 45%) of the title compound as colorless oil.

Workup

  1. customThe cooling bath was removed
  2. customEvaporation of the solvent under reduced pressure
  3. customgave a yellow oil which
  4. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

Sources & evidence

ORD record
ord-311bd5f31668455eb827eba648eda1b0
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

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