Methanol → HCID 178431440, compound

HRID 217911Notes

Reaction equation

HRID 217911 reaction equation
Cl.[OH:2][CH:3]([CH2:31][OH:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]([C:22]2[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=2)=[O:21])=[NH:18])=[CH:8][CH:7]=1.CO.O.[C:36]1(C)[CH:41]=CC(S(O)(=O)=O)=C[CH:37]=1>CC(C)=O>[CH3:37][C:36]1([CH3:41])[O:2][CH:3]([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]([C:22]3[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=3)=[O:21])=[NH:18])=[CH:10][CH:11]=2)[CH2:31][O:32]1

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 178479340HCID 178479340, compound

Product 1

HCID 178431440HCID 178431440, compoundYield 185.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 33 (150 mg, 0.3 mmol) was suspended in dry acetone (50 mL) then methanol was added until a clear solution was formed (approx. 15 mL). p-Toluenesulfonic acid monohydrate (25 mg) was added along with molecular sieves (5 A) and the reaction mixture was stirred for 48 h at room temperature. After this time, the reaction mixture was filtered, silica gel (20 mL) was added and the solvent was removed under reduced pressure. This silica gel with the reaction mixture adsorbed was added to the top of a silica gel flash chromatography column. Compound 37 (120 mg, 81%) was isolated by flash chromatography (silica gel, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.30 (s, 3H), 1.34 (s, 3H), 1.52 (br s, 4H), 2.56 (br s, 2H), 3.13 (br s, 2H), 3.71 (m, 1H), 3.92 (m, 2H), 4.08 (m, 1H), 4.45 (m, 1H), 6.64 (br s, 2H), 6.82 (m, 2H), 7.12 (m, 2H). APCI MS m/z=492 [C22H30ClN7O4+H]+.

Workup

  1. customwas formed (approx. 15 mL)
  2. filtrationAfter this time, the reaction mixture was filtered
  3. additionsilica gel (20 mL) was added
  4. customthe solvent was removed under reduced pressure
  5. additionThis silica gel with the reaction mixture adsorbed was added to the top of a silica gel flash chromatography column

Sources & evidence

ORD record
ord-d4470384676747fe8545eb1f359e4ce7
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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