Acetone → HCID 68753384, compound

HRID 333300Notes

Reaction equation

HRID 333300 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:14][C:15]([C:17]2(CC(Cl)=C)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:3][CH:2]=1.[O:32]=[O+][O-].C[C:36]([CH3:38])=[O:37]>>[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:14][C:15]([C:17]2([CH2:38][C:36]([OH:32])=[O:37])[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 24823OzoneHCID 86665065HCID 86665065, compound

Product 1

HCID 68753384HCID 68753384, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)—N-(3-(biphenyl-4-yl)-1-(dimethylamino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (78 mg, 0.18 mmol) in acetone (5 mL) at −78° C. was bubbled ozone for 1 minutes with a persistent pale blue color. The mixture was stirred at −78° C. for 5 minutes. To the mixture was bubbled oxygen for 10 minutes then added dimethyl sulfide (0.5 mL) followed by 1 mL of water. The mixture was stirred for 1 hr at room temperature and concentrated under reduced pressure. The obtained mixture was diluted in EtOAc and acidified with 1 M HCl. The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN) to give (S)-2-(1-(3-(biphenyl-4-yl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamoyl)cyclopentyl)acetic acid (62 mg). HPLC retention time=1.54 minutes (condition D); MS (m+1)=423.1; 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 1.50-1.76 (m, 6H), 1.86-2.09 (m, 2H), 2.63 (s, 2H), 2.89 (s, 3H), 2.96-3.01 (m, 1H), 2.99 (s, 3H), 3.10 (dd, 1H), 5.00-5.20 (m, 1H), 6.95 (br. s., 1H), 7.31 (d, J=8.1 Hz, 2H), 7.35-7.44 (m, 1H), 7.48 (t, J=7.6 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.62-7.72 (m, 2H).

Workup

  1. customTo the mixture was bubbled oxygen for 10 minutes
  2. stirringThe mixture was stirred for 1 hr at room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained mixture was diluted in EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN)

Sources & evidence

ORD record
ord-aae6ea5e3e7d4569a116121696eb95e2
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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