Benzyl chloroformate → Phenylmethyl N-((1S,2R)-1-(aminocarbonyl)-2-hydroxypropyl)carbamate
Reaction equation
[NH2:1][C@H:2]([C:6]([NH2:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].C(=O)([O-])O.[Na+].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[NH:1]([C:22]([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23])[C@H:2]([C:6]([NH2:8])=[O:7])[C@@H:3]([CH3:5])[OH:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
11.8 g (0.1 mol) of L-threonine amide and 16.8 g (0.2 mol) of sodium hydrogencarbonate were added to 350 ml of water to obtain a solution. 17.9 g (0.105 mol) of benzyloxycarbonyl chloride was added slowly to the solution under vigorous stirring at a temperature of up to 20° C. over a period of 30 min. The mixture was stirred at room temperature for additional 5 h and a solid thus formed was filtered, washed and dried to obtain 21.4 g (yield: 85.0 %) of impure solid Z-L-Thr-NH2. 85 ml of water was added to the solid product and heated to 73° C. to obtain a solution. A small amount of an insoluble matter was filtered out and the filtrate was left to cool to room temperature and then cooled to 10° C. in an ice/water bath. Crystals thus formed were filtered and dried at a temperature of up to 40° C. under an aspirator vacuum to obtain 20.0 g of Z-L-Thr-NH2.1/2H2O. The filtration time was 2 min.
Workup
- customto obtain a solution
- stirringThe mixture was stirred at room temperature for additional 5 h
- customa solid thus formed
- filtrationwas filtered
- washwashed
- customdried
Sources & evidence
- ORD record
- ord-fa0d4275e29c466ebd587b027be4dc14
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628111
Reaction notes
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