Potassium Phosphate, Tribasic → HCID 54539407, compound

HRID 1109797Notes

Reaction equation

HRID 1109797 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl.[NH2:10][C@H:11]([C:17]([O:19][CH3:20])=[O:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14].Br[C:22]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2>C(#N)C>[CH3:20][O:19][C:17](=[O:18])[C@H:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[NH:10][C:33]1[C:34]2[CH:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]=2[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2316249-Bromo-9-phenylfluoreneHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)

Product 1

HCID 54539407HCID 54539407, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of anhydrous Pb(NO3)2 (45.0 g, 138.7 mmol) and anhydrous K3PO4 (75.0 g, 353.3 mmol) in dry acetonitrile (300.0 mL) was added sequentially L-aspartic acid dimethyl ester hydrochloride of Example 1 (32.0 , 161.9 mmol) and 9-bromo-9-phenylfluorene (62.0 g, 193.2 mmol). The mixture which resulted was stirred for 20 h at room temperature and then filtered through celite. The filter cake was washed with chloroform (3×300.0 mL). The combined organic solvents were removed under reduced pressure and the residue oil was partitioned between ether (800.0 mL) and the solution of citric acid (5%, 200.0 mL). The ether layer was removed and the aqueous phase extracted with ether (3×200.0 mL). The combined organic layers were washed with brine (2×150.0 mL), dried (MgSO4) and then removed under reduced pressure. The residue was purified by a flash chromatograph (600.0 g silica gel, EtOAc/hexane, 1/10 to 1/4 ) to provide the product as a pale yellow oil (64.0 g).

Workup

  1. customThe mixture which resulted
  2. filtrationfiltered through celite
  3. washThe filter cake was washed with chloroform (3×300.0 mL)
  4. customThe combined organic solvents were removed under reduced pressure
  5. customthe residue oil was partitioned between ether (800.0 mL)
  6. customThe ether layer was removed
  7. extractionthe aqueous phase extracted with ether (3×200.0 mL)
  8. washThe combined organic layers were washed with brine (2×150.0 mL)
  9. dry with materialdried (MgSO4)
  10. customremoved under reduced pressure
  11. customThe residue was purified by a flash chromatograph (600.0 g silica gel, EtOAc/hexane, 1/10 to 1/4 )

Sources & evidence

ORD record
ord-d506fee999b449ac95c435bc5e8c0638
Source dataset
uspto-grants-1994_06
Patent number
US05322942

Reaction notes

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