p-Toluenesulfonic acid monohydrate → HCID 18337569, compound

HRID 2297984Notes

Reaction equation

HRID 2297984 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:44])[C@H:11]([N:20]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]2[O:41][CH2:42][O:43][C:37]=2[CH:36]=1)[S:21]([C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[CH:26][C:25]=1[CH3:33])(=[O:23])=[O:22])[CH2:12][O:13]C1CCCCO1)[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>CO>[CH2:1]([O:8][NH:9][C:10](=[O:44])[C@H:11]([N:20]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]2[O:41][CH2:42][O:43][C:37]=2[CH:36]=1)[S:21]([C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[CH:26][C:25]=1[CH3:33])(=[O:23])=[O:22])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18337570HCID 18337570, compound

Product 1

HCID 18337569HCID 18337569, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,6-dimethylbenzenesulfonyl)amino]-3-(tetrahydropyran-2-yloxy)propionamide (1.7 g, 4.3 mmol) in methanol (100 mL) at 0° C. was added p-toluenesulfonic acid monohydrate (150 mg). After 12 h, the reaction mixture was warmed to room temperature and stirred for an additional 5 h. The reaction mixture was concentrated and the residue was chromatographed (Biotage 40M; 20% to 50% ethyl acetate-hexanes) to afford N-benzyloxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,6-dimethylbenzenesulfonyl)amino]-3-hydroxypropionamide (1.60 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed (Biotage 40M; 20% to 50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-56fb7b6133d7405d89ac6ce66c4b562c
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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