4-Methylmorpholine → Boc-(D)-Met-(L)-Ala-OMe
Reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:29][O:30][C:31](=[O:35])[C@H:32]([CH3:34])[NH2:33].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>ClCCl>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@@H:9]([C:14]([NH:33][C@H:32]([C:31]([O:30][CH3:29])=[O:35])[CH3:34])=[O:16])[CH2:10][CH2:11][S:12][CH3:13]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Boc-(D)-methionine (50.0 g) is dissolved in dichloromethane (200 ml) and 1-hydroxybenzo-triazole hydrate (29.7 g) and (L)-alanine methyl ester hydrochloride (31.0 g) is added. The mixture is cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (43.0 g) is added in portions, maintaining the temperature of the mixture at 0-5° C. N-Methylmorpholine (42.2 g) is then added over 30 minutes, maintaining the temperature of the mixture at 0-5° C. The mixture is then stirred at 0° C. for 5 hours. The reaction mixture is washed successively with water (2×100 ml), 10% aqueous citric acid solution (100 ml), saturated aqueous sodium bicarbonate solution (100 ml), water (100 ml) and evaporated to dryness at 40° C. under reduced pressure to give Boc-(D)-Met-(L)-Ala-OMe (67.0 g estimated to contain 0.17 mol) as an oil.
Workup
- temperaturemaintaining the temperature of the mixture at 0-5° C
- temperaturemaintaining the temperature of the mixture at 0-5° C
- washThe reaction mixture is washed successively with water (2×100 ml), 10% aqueous citric acid solution (100 ml), saturated aqueous sodium bicarbonate solution (100 ml), water (100 ml)
- customevaporated to dryness at 40° C. under reduced pressure
Sources & evidence
- ORD record
- ord-184297fd148c4f2d9f87bb8c352a0d9b
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248903B1
Reaction notes
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