Water → HCID 59771240, compound

HRID 447967Notes

Reaction equation

HRID 447967 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-4c090362e44e4c87ad3ef17e1f46fae3
Source dataset
uspto-grants-2013_07
Patent number
US08481564B2

Reaction notes

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