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 1064906

반응식

HRID 1064906 반응식
[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

참가 물질

9

반응물 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

생성물 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-one수율 46.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 μmol) 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4d776061f2fc469cba6d3039a012ce61
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969725B2

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