HCID 67588407, compound → HCID 44300540, compound

HRID 1416788Notes

Reaction equation

HRID 1416788 reaction equation
[CH2:1]([O:4][C:5]([C:7]1([C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([N:19]([CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=3)[OH:30])C(OCC(Cl)(Cl)Cl)=O)[CH3:18])=[CH:15][C:9]=2[O:8]1)=[O:6])[CH:2]=[CH2:3]>[Zn].C(O)(=O)C>[CH2:1]([O:4][C:5]([C:7]1([C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([NH:19][CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=3)[OH:30])[CH3:18])=[CH:15][C:9]=2[O:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 67588407HCID 67588407, compound

Product 1

HCID 44300540HCID 44300540, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 370 mg (0.55 mmol) 5-{(2R)-2-[[(2R)-2-(3-chloro-phenyl)-2-hydroxy-ethyl]-(2,2,2-trichloro-ethoxycarbonyl)-amino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diallyl ester, 10 mL glacial acetic acid and 357 mg (5.46 mmol) of Zn dust were stirred at room temperature for 40 h. The reaction mixture was filtered through celite, poured into 50 mL brine, and extracted with 3×50 mL EtOAc. The combined organics were washed with 3×75 mL sat. NaHCO3, 1×75 mL brine, dried over Na2SO4, filtered and evaporated to a colorless oil. Flash chromatography on silica gel, eluting with CHCl3 /MeOH (20/1 to 10/1), gave 180 mg (0.36 mmol, a 66% yield) of the title compound (Rf =0.35; 10/1 CHCl3 /MeOH) as a colorless gum; 1H NMR (300 MHz, CDCl3): δ 1.20-1.33 (m, 3H), 2.70-2.81 (m, 1H), 3.00-3.19 (m, 2H), 3.36-3.45 (m, 2H), 4.50-5.50 (br s, 2H), 4.70-4.80 (m, 4H), 5.10-5.20 (m, 1H), 5.25-5.40 (m, 4H), 5.82-6.00 (complex m, 2H), 6.70-6.91 (m, 3H), 7.17-7.30 (m, 3H), 7.41 (s, 1H); MS (ES) m/z (relative intensity): 502 (M+, 100).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. additionpoured into 50 mL brine
  3. extractionextracted with 3×50 mL EtOAc
  4. washThe combined organics were washed with 3×75 mL sat. NaHCO3, 1×75 mL brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to a colorless oil
  8. washFlash chromatography on silica gel, eluting with CHCl3 /MeOH (20/1 to 10/1)
  9. customgave 180 mg (0.36 mmol

Sources & evidence

ORD record
ord-622c337dc93a42db9327b4535dd24b78
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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