p-Toluenesulfonic acid monohydrate → Adamantane-1-carboxylic acid [3-(2-methoxyethyl)-4,6-dihydro-3H-furo[3,4-d]thiazol-2-ylidene]-amide

HRID 255082Notes

Reaction equation

HRID 255082 reaction equation
C(O[C:4]12[CH2:11][O:10][CH2:9][CH:8]1[S:7]/[C:6](=[N:12]\[C:13]([C:15]13[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]1)[CH2:22]3)=[O:14])/[N:5]2[CH2:25][CH2:26][O:27][CH3:28])C.O.C1(C)C=CC(S(O)(=O)=[O:37])=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:26]([O-:27])(=[O:37])[CH3:25].[NH4+:5].[CH3:28][O:27][CH2:26][CH2:25][N:5]1[C:4]2[CH2:11][O:10][CH2:9][C:8]=2[S:7][C:6]1=[N:12][C:13]([C:15]12[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:23]3)[CH2:22]1)[CH2:24]2)=[O:14]

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178465757HCID 178465757, compound

Product 2

HCID 517165Ammonium AcetateHCID 66858750Adamantane-1-carboxylic acid [3-(2-methoxyethyl)-4,6-dihydro-3H-furo[3,4-d]thiazol-2-ylidene]-amideYield 105%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution the product of Example 72D (15 mg, 0.04 mmol) in toluene (10 mL) was added p-toluenesulfonic acid monohydrate (2 mg). The solution was heated at reflux for 3 hours and then cooled to room temperature, diluted with ethyl acetate, washed with 1M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded 4 mg (30%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.61-1.76 (m, 6 H), 1.82-1.88 (m, 6 H), 1.93-2.02 (m, 3 H), 3.24 (s, 3 H), 3.63 (t, J=5.0 Hz, 2 H), 4.18 (t, J=5.0 Hz, 2 H), 4.91 (s, 4 H); MS (ESI+) m/z 363 (M+H)+;

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. washwashed with 1M aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-a8589fad000642a5879affb57d45312d
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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