Dichloromethane → HCID 11476622, compound

HRID 602691Notes

Reaction equation

HRID 602691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[N:9]2[CH2:12][CH:11]([CH:13]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)[C:14]([CH3:17])(O)[CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.C(Cl)Cl.C(N(S(F)(F)F)CC)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>CCOCC>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:12][CH:11]([C:13]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)=[C:14]([CH3:17])[CH3:15])[CH2:10]2)=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11751892HCID 11751892, compound

Product 1

HCID 11476622HCID 11476622, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 47 mg (0.099 mmol) of 1-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-1-(3,5-difluorophenyl)-2-methylpropan-2-ol in 0.5 mL of CH2Cl2 52 uL (0.395 mmol) of DAST (diethylaminosulfur trifluoride) was added and the solution was stirred for 2 h at −78° C. Then to the reaction mixture was added 10 mL of ether and 3 mL of ag NaHCO3. The pH was adjusted to 8-9 with 2N NaOH. The water layer was extracted with CH2Cl2 (3×10 mL). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as a white solid; 1H NMR (CDCl3) δ 1.51 (s, 3H), 1.71 (s, 3H), 2.60 (t, J=7.8 Hz, 2H), 3.36 (t, J=7.6 Hz, 2H), 3.70 (m, 1H), 4.06 (s, 1H), 6.56 (m, 2H), 6.73 (m, 1H), 7.24 (m, 8H); Mass Spectrum: m/e=458 (M+1 35Cl, 35Cl) and 460 (M+1 35Cl, 37Cl).

Workup

  1. extractionThe water layer was extracted with CH2Cl2 (3×10 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-f643f3cbff824f16b6e03f37ad8886c9
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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