L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 54411304, compound

HRID 487433Notes

Reaction equation

HRID 487433 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][CH2:7][C:8]#[N:9])C.[C:13]([O:17][C:18]([NH:20][C@H:21]([C:29]([OH:31])=O)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:22]([C@H:21]1[C:29](=[O:31])[N:6]([CH2:7][C:8]#[N:9])[CH:5]=[CH:4][N:20]1[C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19094668HCID 19094668, compound

Product 1

HCID 54411304HCID 54411304, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3.0 g of 2,2-diethoxyethylaminoacetonitrile, 4.85 g of N-t-butoxycarbonyl-L-phenylalanine and 50 ml of methylene chloride was added 3.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, which was stirred for 4 hours at room temperature. The reaction mixture was concentrated under reduced pressure. To the concentrate were added 100 ml of ethyl acetate and 50 ml of water. The mixture was shaken. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate and, then, concentrated under reduced pressure. The concentrate (7.0 g) was dissolved in 100 ml of ethyl acetate. To the solution was added 0.5 g of p-toluenesulfonic acid, and the mixture was stirred for 4 hours at 75° to 85° C. The reaction mixture was cooled and washed with an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by means of a silica-gel column chromatography (eluent: hexane-ethyl acetate=3:1), followed by recrystallization from ethyl acetate to afford 3.7 g of colorless prisms, m.p.160°-162° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the concentrate were added 100 ml of ethyl acetate and 50 ml of water
  3. stirringThe mixture was shaken
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationThe concentrate (7.0 g)
  9. dissolutionwas dissolved in 100 ml of ethyl acetate
  10. additionTo the solution was added 0.5 g of p-toluenesulfonic acid
  11. stirringthe mixture was stirred for 4 hours at 75° to 85° C
  12. temperatureThe reaction mixture was cooled
  13. washwashed with an aqueous solution of sodium hydrogencarbonate
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe concentrate was purified by means of a silica-gel column chromatography (eluent: hexane-ethyl acetate=3:1)
  17. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4485e334478346ea91b66fbc0f26605c
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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