p-Toluenesulfonic acid → N-{3-[5-(4-Benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide

HRID 1260506Notes

Reaction equation

HRID 1260506 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:24](OCC)[CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH3:30])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]2[CH2:17][O:18][CH:24]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:16][CH2:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12677171N-(4,4-diethoxybutyl)acetamideHCID 498554052-(4-Benzyloxyphenoxy)propane-1,3-diol

Product 1

HCID 44608467N-{3-[5-(4-Benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-Benzyloxyphenoxy)propane-1,3-diol (98 mg, 0.36 mmol), N-(4,4-diethoxybutyl)acetamide (73.06 mg, 0.36 mmol) and p-toluenesulfonic acid (61.89 mg, 0.36 mmol) were stirred in 6 ml of toluene at 60° C. for 2 h and concentrated. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 30.8 mg (22%) of cis-N-{3-[5-(4-benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide, M+H+: 386.15 and 29.8 mg (22%) of trans-N-{3-[5-(4-benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide, M+H+: 386.19.

Workup

  1. concentrationconcentrated
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-9590bdadaa6f41c687f05661261d4804
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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