Benzyl Chloride → N-tert-butoxycarbonylphenylalanine benzyl ester
Reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[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(=O)([O-])[O-].[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.O>[C:16]([O:15][C:13]([NH:1][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([O:12][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:11])=[O:14])([CH3:19])([CH3:18])[CH3:17]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of Boc-Phe-OH (10 g, 37.7 mmoL) in DMF (50 mL) was added potassium carbonate (7.81 g, 56.5 mmol) followed by benzyl chloride (4.55 mL, 39.6 mmol) and the resulting suspension was stirred at 60° C. for 3 d. The mixture was diluted with water (400 mL) and extracted with ethyl acetate (75 mL, 2×25 mL). The combined organics were washed with brine (200 mL), water (3×100 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated then chromatographed on silica gel eluting with 0%-20% ethyl acetate in hexanes. The product-containing fractions were concentrated in vacuo giving the title compound (12.84 g, 95%) as a white solid.
Workup
- extractionextracted with ethyl acetate (75 mL, 2×25 mL)
- washThe combined organics were washed with brine (200 mL), water (3×100 mL) and brine (50 mL)
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthen chromatographed on silica gel eluting with 0%-20% ethyl acetate in hexanes
- concentrationThe product-containing fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-f0611ac2526e48c0aadda61bc3fc210e
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09441012B2
Reaction notes
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