Benzyl chloroformate → N-(Benzyloxycarbonyl)-D-phenylalanine
Reaktionsgleichung
[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.[OH-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>>[CH2:19]([O:18][C:16]([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:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Komponenten
Versuchsvorschrift
A 15.0 g sample of D-phenylalanine was dissolved in 45 ml of aqueous solution containing 7.26 g of 50% sodium hydroxide. This solution was stirred at 0°-10° C. as 16.3 g of benzyl chloroformate was added rapidly in portions. The resulting reaction was mildly exothermic, and shortly after addition, solids precipitated. An additional 45 ml of water and 3.63 g of 50% sodium hydroxide were added, causing most of the solids to redissolve. The reaction mixture was stirred for 20 minutes and then acidified with 6 N hydrochloric acid. The resulting solids were filtered, washed with water and then with hexane, and dried by suction and then under vacuum to give 47 g of white solids. These solids dissolved in ether were washed twice with 1 N hydrochloric acid and then with water, dried over MgSO4 and stripped to 35° C. at 2.5 mm Hg to give 27.7 g of the desired product as a colorless oil.
Aufarbeitung
- additionwas added rapidly in portions
- customThe resulting reaction
- additionshortly after addition, solids
- customprecipitated
- additionAn additional 45 ml of water and 3.63 g of 50% sodium hydroxide were added
- dissolutionto redissolve
- filtrationThe resulting solids were filtered
- washwashed with water
- dry with materialwith hexane, and dried by suction
Quellen und Nachweise
- ORD-Eintrag
- ord-56dc96adec5f483abeda4e4025c4eeb2
- Quelldatensatz
- uspto-grants-1985_07
- Patentnummer
- US04529810
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