Benzyl chloroformate → N-(Benzyloxycarbonyl)-D-phenylalanine
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.[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]=1Participants
Procedure
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 6N 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 1N 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.
Workup
- 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
Sources & evidence
- ORD record
- ord-b0f530ecfa2e4d0ba8b8c22d72a73919
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04582646
Reaction notes
Loading…