Triphenylphosphine → 5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one

HRID 1167424

반응식

HRID 1167424 반응식
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH:16]=3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1.O[C:30]1[CH:34]=[CH:33][O:32][N:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[O:32]1[CH:33]=[CH:34][C:30]([O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH2:20][CH2:19][N:18]([CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:17][CH:16]=4)=[C:11]([F:28])[CH:10]=3)[CH2:4]2)=[N:31]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11668069(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-hydroxymethyl-oxazolidin-2-oneHCID 178516613HCID 178516613, 화합물

생성물 1

HCID 213566645(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Prepared by the general method of Example 1 using as starting material 5(R)-hydroxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one (WO97/30995; 4.0 g, 10.5 mmol), 3-hydroxyisoxazole (1.0 g, 11.8 mmol), triphenylphosphine (3.24 g, 12.4 mmol) and diisopropylazodicarboxylate (2.36 g, 11.7 mmol) in tetrahydrofuran (60 ml). Purified by flash chromatography (Merck 9385 silica; tert-butyl methyl ether/EtOAc/MeOH (70:30:0.5) eluant) to give the product (3.0 g, 64%) as a colourless crystalline solid. MS: ESP30 (M+H)+=450.

후처리

  1. customPrepared by the general method of Example 1 using
  2. customPurified by flash chromatography (Merck 9385 silica; tert-butyl methyl ether/EtOAc/MeOH (70:30:0.5) eluant)

출처 및 근거

ORD 기록
ord-104416dacc8c4f9d8f9cf75ea97e9529
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617339B1

연결된 노트

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