Monobasic potassium phosphate → 9-carboxynonyl 5-(Boc-amino)-4-oxopentanoate

HRID 1771054Notes

Reaction equation

HRID 1771054 reaction equation
P([O-])(O)(O)=O.[K+].[C:7]([NH:14][CH2:15][C:16](=[O:39])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC(Cl)(Cl)Cl)=[O:32])=[O:20])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>O1CCCC1.[Zn]>[C:7]([NH:14][CH2:15][C:16](=[O:39])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:20])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphate3×HCID 900345582,2,2-trichloroethyl 10-[5-(Boc-amino)-4-oxopentanoyloxy]decanoate

Product 1

HCID 900345709-carboxynonyl 5-(Boc-amino)-4-oxopentanoateYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

One molar potassium dihydrogen phosphate (KH2PO4) solution (4.0 mL; 4.0 mmol) followed by zinc powder (2.0 g; 30 mmol) was added to a stirred solution of the product from 12b (1.50 g; 2.8 mmol) in tetrahydrofuran (25 mL). After stirring 18 h at ambient temperature, a new portion of 1 M KH2PO4 solution (5 mL) and zinc (2.0 g; 30 mmol) was added. Additional 1 M KH2PO4 solution (25 mL) was added after 5 h and the mixture was stirred overnight at ambient temperature. The mixture was vacuum filtered and the residue was washed with ethyl acetate. Ethyl acetate in the filtrate was evaporated off and the aqueous solution was extracted with dichloromethane (4×5 mL). The combined extracts were dried (Na2SO4), filtered, and evaporated. 1.04 g (93%) product was obtained (pale yellow waxy solid).

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. filtrationfiltered
  3. washthe residue was washed with ethyl acetate
  4. customEthyl acetate in the filtrate was evaporated off
  5. extractionthe aqueous solution was extracted with dichloromethane (4×5 mL)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-58af213c82894f3c8e7b36867e830929
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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