Magnesium monoperoxyphthalic acid → HCID 178499278, compound

HRID 1808011Notes

Reaction equation

HRID 1808011 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][C:9]=1[N:10]([C:17]([C@H:19]1[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18])[CH:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1)=[O:4].C(OO)(=O)C1C(=CC=CC=1)C(O)=[O:36].[Mg]>CCO.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:8][C:9]=1[N:10]([C:17]([C@H:19]1[CH2:20][CH2:21][C@H:22]([CH3:25])[CH2:23][CH2:24]1)=[O:18])[CH:11]1[CH2:16][CH2:15][S:14](=[O:36])[CH2:13][CH2:12]1)=[O:4]

Participants

5

Reactant 2

HCID 9815656Magnesium monoperoxyphthalic acidHCID 178499277HCID 178499277, compound

Product 1

HCID 178499278HCID 178499278, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-[(trans-4-methyl-cyclohexanecarbonyl)-(tetrahydro-thiopyran-4-yl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (57 mg, 0.124 mmol)in EtOH (1.2 mL) from step 2 was added magnesium monoperoxyphthalic acid (29.6 mg, 0.06 mmol) in one portion, stirred for 24 h. Reaction mixture was diluted with water, extracted with EtOAc. The combined organic solution was washed with brine, dried, and concentrated. Purification of the residue on Preparative TLC using 5% MeOH-DCM gave 3-[(trans-4-methyl-cyclohexanecarbonyl)-(1-oxo-tetrahydro-thiopyran-4-yl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (30 mg, 51%). NMR 1H (CDCl3, 400 MHz, For major isomer): 7.66-7.6 (m, 2H), 7.5-7.4 (m, 3H), 7.09 (s, 1H), 4.84-4.76 (t, 1H), 3.85 (s, 3H), 3.4-1.2 (m), 0.772 (d, J=6.6, 3H), 0.74-0.56 (m, 2H).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic solution was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification of the residue on Preparative TLC

Sources & evidence

ORD record
ord-ff42043f41d24f448abfd5b012cd77c5
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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