Sodium Bicarbonate → D-Homophenylalanine Benzyl ester
Reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:31])[C@@H:21]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[CH2:12]([O:19][C:20](=[O:31])[C@@H:21]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:22])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
D-Homophenylalanine Benzyl ester Tosylate (2.48 g, 5.6 mmol) was suspended in ethyl acetate (25 mL) and a saturated solution of sodium bicarbonate in water was added in portions (25 mL) with stirring at 25° C. The water layer was extracted with ethyl acetate (3×10 mL). The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford D-Homophenylalanine Benzyl ester. The ester was dissolved in acetonitile (25 mL). NaNd-bis-Boc-L-Ornithine (2.0 g, 6.0 mmol) was then added followed by N-hydroxysuccinimide (50 mg) and dicyclohexylcarbodiimide (1.28 g, 6.2 mmol). The reaction was stirred at 25° C. for 30 hr, filtered and the filtrate concentrated to dryness to afford crude product. It was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1), which gave the title product (2.80 g) as white solid.
Workup
- extractionThe water layer was extracted with ethyl acetate (3×10 mL)
- extractionThe combined organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-e1f3febee43941949c08619364c34604
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893020B2
Reaction notes
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