Triethylamine → {4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}-1-(4-chlorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

HRID 603926

反応式

HRID 603926 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13]SC3C([N+]([O-])=O)=CC=CN=3)[C@H:9]2[C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:58]1[C:62]2[CH:63]=[CH:64][C:65]([C:67](=[O:70])[CH2:68]Br)=[CH:66][C:61]=2[O:60][CH2:59]1.CCN(CC)CC>CC(C)=O.C(Cl)Cl.O>[O:58]1[C:62]2[CH:63]=[CH:64][C:65]([C:67](=[O:70])[CH2:68][S:13][C@H:10]3[C:11](=[O:12])[N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C@@H:9]3[C:24]3[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:25]=3)=[CH:66][C:61]=2[O:60][CH2:59]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 2437771-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-oneHCID 86643081HCID 86643081、化合物

生成物 1

HCID 67270870{4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}-1-(4-chlorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl (4-{(2R,3R)-1-(4-chlorophenyl)-3-[(3-nitropyridin-2-yl)dithio]-4-oxoazetidin-2-yl}phenoxy)acetate (Method 27) (0.70 g, 1.22 mmol) was dissolved in acetone (30 mL) at room temperature, then water (10 mL) and triphenyl phosphine (0.32 g, 1.22 mmol) was added. The mixture was stirred at room temperature for 15 minutes and then concentrated under reduced pressure to afford the crude thiol as a brown oil. This crude thiol was immediately dissolved in CH2Cl2 (30 mL) and 1-benzo[1,3]dioxol-5-yl-2-bromo-ethanone (0.59 g, 2.44 mmol) was added, followed by Et3N (0.34 mL, 2.44 mmol). The mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash-chromatography (Heptane:EtOAc 7:3 and then 2:1). The resulting product (0.90 g) was dissolved in 15 ml formic acid and stirred at room temperature for 3 hours. Concentration under reduced pressure and purification by flash-chromatography afforded the title compound.

後処理

  1. concentrationconcentrated under reduced pressure
  2. customto afford the crude thiol as a brown oil
  3. stirringThe mixture was stirred at room temperature for 18 hours
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash-chromatography (Heptane:EtOAc 7:3
  6. dissolutionThe resulting product (0.90 g) was dissolved in 15 ml formic acid
  7. stirringstirred at room temperature for 3 hours
  8. concentrationConcentration
  9. customunder reduced pressure and purification by flash-chromatography

出典と根拠

ORDレコード
ord-d33d4c7d09b5497fabebe5f35fbcdc9e
出典データセット
uspto-grants-2011_03
特許番号
US07906502B2

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