L-Phenylalanine → 2768-53-8

HRID 1086312Notes

Reaction equation

HRID 1086312 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]([O:16][CH2:17][CH3:18])(=[O:15])C>C(=O)([O-])[O-].[K+].[K+].C(#N)C.Cl>[CH2:17]([O:16][C:13]([NH:1][C@H:2]([C:10]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:11])[CH3:3])=[O:15])[C:18]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 6140L-PhenylalanineHCID 8857Ethyl Acetate

Product 1

HCID 69991262768-53-8Yield 39%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent2×HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of L-phenylalanine (0.33 g, 2.0 mmol) in 0.20M potassium carbonate (20 mL) and acetonitrile (30 mL) was added dropwise a solution of N-benzyloxycarbonyl-L-alanine N-carboxyanhydride (0.45 g, 1.8 mmol) in acetonitrile (5 mL) at 0° C. The mixture was stirred 40 min at 0° C. and diluted with ethyl acetate (50 mL) and 1M hydrochloric acid (10 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (2×35 mL). The combined organic fractions were washed with brine (30 mL), 0.5M hydrochloric acid (2×50 mL) and water (2×50 mL), dried (MgSO4) and concentrated. The residue was recrystallized from chloroform/hexane to give 0.26 g (39%) of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine: mp 121°-122° C.; NMR (DMSO-d6) δ 12.71 (s, 1 H), 8.06 (m, 1 H), 7.30 (m, 5 H), 5.01 (s, 2 H), 4.43 (m, 1 H), 4.06 (m, 1 H), 2.99 (m, 2 H), 11.19 (d, 2 H, J=7 Hz).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate (2×35 mL)
  3. washThe combined organic fractions were washed with brine (30 mL), 0.5M hydrochloric acid (2×50 mL) and water (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-9b2d8df70e6f4ea1b5cbeb3358ed97fc
Source dataset
uspto-grants-1991_07
Patent number
US05028693

Reaction notes

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