Triethylamine → L-Leucine
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CCN(CC)CC>C(O)C>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
The Merrifield resin (2.1 g) was suspended in 30 ml of ethanol. A solution of 0.70 g (2.71 mM) of Boc-Leu and 0.9 equivalent of Et3N (2.43 mM, 0.34 ml) in 3 ml of ethanol was added to the resin suspension. The mixture was stirred slowly at 90° C. under anhydrous conditions for 24 hours using a magnetic stirrer. The esterified resin was washed successively with EtOH, H2O, MeOH and CH2Cl2 ; floated 3 times with CH2Cl2 to get rid of fine resin particles; and dried in vacuo over P2O5. Amino acid analysis gave a value of 0.25 mM of Leu/g of substituted resin.
Workup
- washThe esterified resin was washed successively with EtOH, H2O, MeOH and CH2Cl2
- customto get rid of fine resin particles
- dry with materialand dried in vacuo over P2O5
Sources & evidence
- ORD record
- ord-c3393beaab084a37915b23eb31547573
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04110321
Reaction notes
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