Hydrochloric Acid → (5R)-3-(4-{1-[(2S)-2,3-Dihydroxypropanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-3,5-difluorophenyl)-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1452604ノート

反応式

HRID 1452604 の反応式
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][N:28]5[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]5)[O:24][C:23]4=[O:34])=[CH:17][C:16]=3[F:35])[CH2:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.Cl.C(OCC)(=O)C>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:10][CH:11]=[C:12]([C:15]2[C:20]([F:21])=[CH:19][C:18]([N:22]3[CH2:26][C@H:25]([CH2:27][N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]4)[O:24][C:23]3=[O:34])=[CH:17][C:16]=2[F:35])[CH2:13][CH2:14]1)=[O:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57527013HCID 57527013、化合物2 回

生成物 1

HCID 10344340(5R)-3-(4-{1-[(2S)-2,3-Dihydroxypropanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-3,5-difluorophenyl)-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one収率 50.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(5R)-3-[4-(1-{[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]carbonyl}-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Intermediate 55) (542 mg, 1.08 mmol) was dissolved in tetrahydrofuran (20 ml). A solution of hydrochloric acid (1N, 10 ml) was added and the reaction mixture was stirred at room temperature. After 64 hours, the solution was poured into ethyl acetate the aqueous was extracted with ethyl acetate. The aqueous was basified with a solution of 10% aqueous sodium acetate and re-extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrated under vacuum. Chromatography on silica gel with 10% methanol in ethyl acetate gave 254 mg of the title product.

後処理

  1. extractionaqueous was extracted with ethyl acetate
  2. extractionre-extracted with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-f62889baa39d47538d91e8c6fd9c1ce9
出典データセット
uspto-grants-2009_01
特許番号
US07473699B2

反応ノート

読み込み中…