3-Amino-1-propanol → 71347-90-5

HRID 1387252Notes

Reaction equation

HRID 1387252 reaction equation
[CH2:1](CO)[CH2:2][NH2:3].[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:20]12([CH2:30]S(O)(=O)=O)C(C)(C)[CH:24]([CH2:25][CH2:26]1)[CH2:23][C:21]2=O.[C:35](=O)([OH:37])[O-:36].[Na+]>O1CCOCC1.CN(C=O)C.CS(C)=O>[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][O:19][CH2:1][CH2:2][NH:3][C:35]([O:37][CH2:30][C:20]1[CH:21]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:36])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 90863-Amino-1-propanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 516892Sodium Bicarbonate

Product 1

HCID 309084971347-90-5

Reagents, catalysts & solvents 1

HCID 86757220HCID 86757220, compoundSolvent

Procedure

The propanolamine compound prepared above (1.0 eq), N-(benzyloxycarbonyl)ethanolamine (25 eq) and camphorsulfonic acid (1.0 eq) are dissolved in a small amount of dioxane-DMF-DMSO (10:2:1) and stirred at room temperature for about 24 hours. The mixture is neutralized by the addition of aqueous sodium bicarbonate and purified by preparative HPLC (C18 “ZORBAX”, step gradient starting at 70/30:H2O/CH3CN/0.1% TFA). The appropriate fractions are combined, frozen and lyophilized to give solid (MW=1621.66).

Workup

  1. custompurified by preparative HPLC (C18 “ZORBAX”, step gradient starting at 70/30:H2O/CH3CN/0.1% TFA)
  2. temperaturefrozen
  3. customto give solid (MW=1621.66)

Sources & evidence

ORD record
ord-24f0246d17ef4387b2f4f1c609615fb6
Source dataset
uspto-grants-2001_07
Patent number
US06268338B1

Reaction notes

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