Triethylamine → (S)-3-(isopropoxycarbonyl-aminomethyl)-5-methyl-hexanoic acid
Reaction equation
[CH:1]([O:4][C:5]([CH:7]([NH2:17])[CH:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C>O.C(O)(C)C>[CH:1]([O:4][C:5]([CH:7]([NH2:17])[C@@H:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2]Participants
4
Conditions
- Temperature
- 57.5 °C
Procedure
A 500 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with raceme 3-(isopropoxycarbonyl-amino-methyl)-5-methyl-hexanoic acid (44.2 g, 0.180 moles), triethylamine (8.20 g, 0.081 moles) and (S)-(−)-phenyl-ethylamine (12.00 g; 0.099 moles) in a 95:5 water/isopropanol mixture (200 ml) heated at 55-60° C. The mixture is spontaneously left to cool to room temperature, then it is cooled to 0-5° C. for at least 1 h. The solid is filtered off and washed with cool water (2×20 ml) and then with cool toluene (4×20 ml), it is dried in oven at 55-60° C. for 16-18 h. 27.0 g of white solid are obtained with an enantiomer ratio of 99:1.
Workup
- waitThe mixture is spontaneously left
- temperatureto cool to room temperature
- temperatureit is cooled to 0-5° C. for at least 1 h
- filtrationThe solid is filtered off
- washwashed with cool water (2×20 ml)
- dry with materialwith cool toluene (4×20 ml), it is dried in oven at 55-60° C. for 16-18 h
Sources & evidence
- ORD record
- ord-045b0b793f3a4b92b51534b38c469830
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063244B2
Reaction notes
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