Thioanisole → Methyl 2-(2-hydroxy-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454701Notes

Reaction equation

HRID 454701 reaction equation
C1(SC)C=CC=CC=1.C([O:16][C:17]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][S:48][CH2:47][CH2:46]2)=[CH:38][C:18]=1[C:19]([NH:21][C:22]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:20])C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:16][C:17]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][N:45]2[CH2:46][CH2:47][S:48][CH2:49][CH2:50]2)=[CH:38][C:18]=1[C:19]([NH:21][C:22]1[CH:31]=[C:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:20]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 66990890Methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508814Methyl 2-(2-hydroxy-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoateYield 79.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Thioanisole (3.2 mL) and trifluoroacetic acid (10 mL) were added to the obtained methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate (0.80 g), followed by stirring at room temperature for 18 hours. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 70-0% hexane/ethyl acetate to 100-95% chloroform/methanol] to obtain 0.54 g of methyl 2-(2-hydroxy-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate as a brown solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 70-0% hexane/ethyl acetate to 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-3bd01008ac504e35ac4d03a0fef64601
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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