HCID 9815656, compound → HCID 178499278, compound

HRID 73207Notes

Reaction equation

HRID 73207 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 9815656HCID 9815656, compoundHCID 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-97cb121c146148369c1676d689ef3a7d
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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