Hydrochloric Acid → HCID 178445740, compound

HRID 2389110Notes

Reaction equation

HRID 2389110 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]2([NH:26]S(C(C)(C)C)=O)[CH2:25][O:24][CH2:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.Cl.CCOCC>C1CCCCC1>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]2([NH2:26])[CH2:23][O:24][CH2:25]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67413196HCID 67413196, compound

Product 1

HCID 178445740HCID 178445740, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid {3-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-oxetan-3-yl}-amide (86 mg, 0.19 mmol) in methylene chloride (2 mL, 30 mmol) was added 2.0 M of hydrogen chloride in ether (0.188 mL, 0.376 mmol) and was stirred 10 min. A precipitate formed and cyclohexane was added to dilute the mixture. After removal of solvent, the residue was dissolved in methylene chloride, 1 M aq. NH4OH was added and the extracted organic layer was dried and chromatographed with MeOH/CH2Cl2 (20-40%) to give 3-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)oxetan-3-amine as a solid (44.8 mg, 67%). LCMS: Rf=1.55 min 337.20 ([M-16]). 1H NMR (400 MHz, CHLOROFORM-d) δ=7.84 (d, J=1.4 Hz, 1 H), 7.81-7.70 (m, 2 H), 7.66 (d, J=1.9 Hz, 1 H), 7.22-7.12 (m, 2 H), 5.09 (d, J=6.7 Hz, 2 H), 4.81 (d, J=6.7 Hz, 2 H), 4.29 (tt, J=4.2, 10.8 Hz, 1 H), 2.29 (d, J=13.2 Hz, 2 H), 1.91 (d, J=12.5 Hz, 2 H), 1.56-1.39 (m, 2 H), 1.29-1.02 (m, 3 H), 0.91 (s, 9 H).

Workup

  1. customA precipitate formed
  2. additionto dilute the mixture
  3. customAfter removal of solvent
  4. dissolutionthe residue was dissolved in methylene chloride
  5. addition1 M aq. NH4OH was added
  6. customthe extracted organic layer was dried
  7. customchromatographed with MeOH/CH2Cl2 (20-40%)

Sources & evidence

ORD record
ord-7ecfb5ad96944c5784a8c195004ac2cc
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

Loading…