p-Toluenesulfonic acid → HCID 118199438, compound

HRID 2279987Notes

Reaction equation

HRID 2279987 reaction equation
[O:1]1CCCOC1.[Cl:7][C:8]1[CH:31]=[CH:30][C:11](/[CH:12]=[CH:13]/[C@@H:14]2[CH:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18]CC(C)(C)[O:15]2)=[CH:10][CH:9]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[Cl:7][C:8]1[CH:31]=[CH:30][C:11](/[CH:12]=[CH:13]/[C@@H:14]([OH:15])[CH:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18][OH:1])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104501,3-DioxaneHCID 131733499HCID 131733499, compound

Product 1

HCID 118199438HCID 118199438, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Dioxane, 2-boc amino (10C) (18 mg, 0.05 mmol) and 10 mol % TsOH (1.0 mg, 0.005 mmol) were combined in 5.0 mL 80% EtOH (in H2O) and stirred at reflux for 1 h, until the starting material was consumed as indicated by TLC (5:3/CH2Cl2:EtOAc). The reaction mixture was quenched with 5% NaHCO3, and removed in vacuo. Purification by flash column chromatography on silica gel afforded the desired product as a white solid (92%).

Workup

  1. temperatureat reflux for 1 h, until the starting material
  2. customwas consumed
  3. customThe reaction mixture was quenched with 5% NaHCO3
  4. customremoved in vacuo
  5. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0120ea64dfb64b2fb8a5db945c8d3b9c
Source dataset
uspto-grants-2015_09
Patent number
US09133488B2

Reaction notes

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