Water → HCID 59771240, compound

HRID 340539Notes

Reaction equation

HRID 340539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.[CH2:13]1[CH2:17]OC[CH2:14]1.O.[C:19]([O-:22])([O-])=[O:20].[Na+].[Na+].[CH3:25]COC(C)=O>[Cl-].[Na+].O>[C:13]([O:22][C:19](=[O:20])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:11][OH:12])[CH2:9][OH:10])=[CH:6][CH:7]=1)([CH3:14])([CH3:17])[CH3:25]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 195939762-(4-Aminophenyl)propane-1,3-diol

Product 1

HCID 59771240HCID 59771240, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-(4-amino-phenyl)-propane-1,3-diol (1.6 g, 9.6 mmol, J. Med. Chem., 40(25), 4030-4052, (1997)), di-tert-butyl dicarbonate (BOC)2O (2.30 g, 10.5 mmol), THF (200 mL), water (100 mL) and Na2CO3 (1.12 g, 10.5 mmol) was stirred at RT overnight. The reaction mixture was diluted with EtOAc (200 mL) and satd brine (200 mL). The organic layer was separated and the aq layer was extracted with EtOAc (2×100 mL). The organic layers were combined, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (20-100% EtOAc-hexane) to obtain the title compound (1.2 g, 47%): Mass spectrum (ESI, m/z): Calcd. for C14H21NO4, 290.3 (M+Na). found 290.0.

Workup

  1. customThe organic layer was separated
  2. extractionthe aq layer was extracted with EtOAc (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customwas purified on silica (20-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-32a1e1e84bed49fdb59e8d54a8549622
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

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