p-Toluenesulfonic acid monohydrate → HCID 58009754, compound

HRID 2114831Notes

Reaction equation

HRID 2114831 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([N:15]([CH2:17][CH:18](OC)OC)[CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH:18]=[CH:17][N:15]([CH3:16])[C:13](=[O:14])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58009747HCID 58009747, compound

Product 1

HCID 58009754HCID 58009754, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N2-benzyloxycarbonyl-N1-(2,2-dimethoxyethyl)-N1-methylglycinamide (1.9 Kg, 6.1 mol) and p-toluenesulfonic acid monohydrate (270 g) in toluene (29.4 L) was stirred at 80° C. for 4 hrs. The resultant reaction mixture was cooled to room temperature, washed with water (4×2 L), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residual solid was subjected to column chromatography on silica gel eluting with heptane-ethyl acetate. Concentration of appropriate fractions provide the cyclization product as off-white solid.

Workup

  1. customThe resultant reaction mixture
  2. washwashed with water (4×2 L)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-686515c04c614de0a260f81fc9072607
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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