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Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(1,2,5-thiadiazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167494
ノート
印刷プレビュー

反応式

HRID 1167494 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH2:30][CH2:31][O:32][CH2:33][CH:34]=3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1.O[C:37]1[CH:41]=[N:40][S:39][N:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[S:39]1[N:40]=[CH:41][C:37]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH2:30][CH2:31][O:32][CH2:33][CH:34]=4)=[C:25]([F:35])[CH:24]=3)[CH2:18]2)=[N:38]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 186848415(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-oneHCID 178516825HCID 178516825、化合物

生成物 1

HCID 497388(5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(1,2,5-thiadiazol-3-yloxymethyl)oxazolidin-2-one収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisopropylazodicarboxylate (0.22 g, 1.1 mmol) was added dropwise at ambient temperature to a stirred solution of 5(R)-hydroxymethyl-3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one (WO97/09328; 0.275 g, 0.93 mmol), 3-hydroxy1,2,5-thiadiazole (Weinstock et al. Journal of Organic Chemistry 32, 2823 [1967]; 0.1 12 g, 1.1 mmol) and triphenylphosphine (0.288 g, 1.1 mmol) in dry THF (7 ml). The solution was kept for 1.5 hours. Solvent was evaporated and the residue was purified by flash column chromatography, eluting with EtOAc/isohexane (1:1) to give the title product (0.256 g , 73%) as a solid (mp 146-148 ° C.). MS: 378 (MH+); NMR: 2.4 (1H, bs); 3.78 (3H, t); 3.96 (1H, m); 4.2 (3H, m); 4.66 (2H, m); 5.1 (1H, m); 6.05 (1H, s); 7.27-7.5 (3H, m); 8.41 (1H, s).

後処理

  1. customSolvent was evaporated
  2. customthe residue was purified by flash column chromatography
  3. washeluting with EtOAc/isohexane (1:1)

出典と根拠

ORDレコード
ord-d5d6fc2d4e0648e9a2c190ca483d8838
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06617339B1

反応ノート

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