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 603926Notes

Reaction equation

HRID 603926 reaction equation
[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

Participants

8

Reactant 4

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

Product 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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d33d4c7d09b5497fabebe5f35fbcdc9e
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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