3,4-dihydro-2H-pyran → HCID 178499316, compound

HRID 2099667Notes

Reaction equation

HRID 2099667 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])[C@H:20]1[CH2:21][CH2:22][C@H:23]([O:26][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[CH2:24][CH2:25]1)=[O:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 178499317HCID 178499317, compound

Product 1

HCID 178499316HCID 178499316, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (140 mg, 0.37 mmol) in DCM (4 mL) p-toluenesulfonic acid monohydrate (6 mg) and 3,4-dihydro-2H-pyran (38 μl, 0.42 mmol) were added at room temperature. After stirring for 1 h and min saturated NaHCO3 was added. It was extracted with DCM, washed with brine, dried (MgSO4) and evaporated. The crude material was chromatographed over silica gel (prewashed with Et3N) (hexane:EtOAc—9:1 as eluent) yielding pure 3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (83 mg, 48%).

Workup

  1. extractionIt was extracted with DCM
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude material was chromatographed over silica gel (prewashed with Et3N) (hexane:EtOAc—9:1 as eluent)

Sources & evidence

ORD record
ord-f184055b2f1d4ceba73cd83d9eaae8f3
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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