Thiourea → HCID 24984261, compound

HRID 1710403Notes

Reaction equation

HRID 1710403 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][C:22]4([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[O:21][C:20]3=[O:29])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH:2]=C.NC(N)=S.C(Cl)Cl.C[OH:38]>C(=O)=O.CC(C)=O>[O:29]=[C:20]1[N:19]([CH2:18][C:15]2[CH:14]=[CH:13][C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][O:4][CH2:1][CH:2]=[O:38])=[CH:11][CH:10]=3)=[CH:17][CH:16]=2)[CH2:23][C:22]2([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[O:21]1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 21226129Dichloromethane methanolHCID 24983795HCID 24983795, compound

Product 1

HCID 24984261HCID 24984261, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 18522661Acetone cardiceSolvent

Procedure

3-(4′-Allyloxymethyl-biphenyl-4-ylmethyl)-1-oxa-3-aza-spiro[4.5]decan-2-one (200 mg, 0.51 mmol) was dissolved in DCM/methanol (4:1, 7.5 mL) and was cooled to −78° C. in dry ice-acetone bath. O3 was bubbled through the solution for 15 min. Thin layer chromatography (TLC) confirmed the completion of the reaction at this stage. Thiourea was added to the reaction mixture and stirred at low temperature for 0.5 hr. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature, and stirred overnight. The reaction mixture was concentrated, and the residue was purified on silica gel eluting with 5˜20% ethyl acetate in hexane to give the product as a white solid (80 mg, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 9.76 (s, 1H), 7.63 (m, 4H), 7.44 (d, 2H), 7.35 (d, 2H), 4.7 (s, 2H), 4.47 (s, 2H), 4.16 (s, 2H), 3.14 (s, 2H), 1.78 (m, 4H), 1.45 (m, 6H).

Workup

  1. customO3 was bubbled through the solution for 15 min
  2. customthe completion of the reaction at this stage
  3. customThe cooling bath was removed
  4. stirringstirred overnight
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified on silica gel eluting with 5˜20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0bb5f8ead69d487f95f0a3045070a4f9
Source dataset
uspto-grants-2010_09
Patent number
US07790717B2

Reaction notes

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