3,4-dihydro-2H-pyran → HCID 69103358, compound

HRID 2220388Notes

Reaction equation

HRID 2220388 reaction equation
[CH2:1]([N:8]([CH2:30][C@H:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:39]1[CH:44]=[CH:43][CH2:42][CH2:41][CH2:40]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([N:8]([CH2:30][C@@H:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:38][CH:40]1[CH2:41][CH2:42][CH2:43][CH2:44][O:39]1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 69103326HCID 69103326, compound

Product 1

HCID 69103358HCID 69103358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4′-[2-[benzyl[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-nitro-4-biphenylcarboxylate (2.31 g) in methylene chloride (35 ml) were added dihydropyran (1.24 ml) and pyridinium p-toluenesulfonate (1.36 mg) and stirred overnight at room temperature. The mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution twice and brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-amino]ethyl]-3-nitro-4-biphenylcarboxylate (1.48 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution twice
  3. dry with materialbrine, dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-bda42b7422cf4ffd9e7dbbc7c0a11d96
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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