p-Toluenesulfonic acid monohydrate → HCID 136085222, compound

HRID 1893189Notes

Reaction equation

HRID 1893189 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:35])[CH:9]([C:23]1[NH:24][C:25](=[O:34])[C:26]([OH:33])=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:28]=1)[CH2:10][CH2:11][C:12]([CH3:22])([CH3:21])[CH2:13][O:14]C1CCCCO1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:5][C:6]([N:8]([CH3:35])[CH:9]([C:23]1[NH:24][C:25](=[O:34])[C:26]([OH:33])=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:28]=1)[CH2:10][CH2:11][C:12]([CH3:22])([CH3:21])[CH2:13][OH:14])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136085217HCID 136085217, compound

Product 1

HCID 136085222HCID 136085222, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the crude methyl 2-[1-[(tert-butoxycarbonyl)(methyl)amino]-4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentyl]-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (32 g) and 1 g of p-toluenesulfonic acid monohydrate was dissolved in methanol (100 mL) and stirred at room temperature for 2 hours. The reaction was quenched with 3 mL of saturated NaHCO3 and concentrated. The residue was taken up in 500 mL of EtOAc, washed with saturated NaHCO3 and dried over Na2SO4. Removal of solvents under reduced pressure gave the title product as a brown foam: MS (ES+): 314.1 (M+H).

Workup

  1. customThe reaction was quenched with 3 mL of saturated NaHCO3
  2. concentrationconcentrated
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. customRemoval of solvents under reduced pressure

Sources & evidence

ORD record
ord-29894884f88340c9904d8ace75cd8ad0
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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