Triethylamine → methyl (2S)-2-amino-4-(methylsulfanyl)butanoate
Reaction equation
N1C=CC=C(OCC2C=CC(C(O)=O)=C(C3C=CC=CC=3C)C=2)C=1.ON1C(=O)C2C=CC=CC=2N=N1.Cl.[CH3:38][O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH2:44][S:45][CH3:46])[NH2:42].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:38][O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH2:44][S:45][CH3:46])[NH2:42]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
The 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid prepared in Example 204E (153 mg, 0.48 mmol) was dissolved in 2 mL of DMF and 3-hydroxy1,2,3-benzotriazin-4(3H)-one (39 mg, 0.24 mmol) was added followed by methionine methyl ester HCl (48 mg, 0.24 mmol), (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg, 0.24 mmol) and triethylamine (0.03 mL, 0.32 mmol) and the reaction mixture was stirred for 16 hours at 25° C. The reaction mixture was taken up in ethyl acetate and washed three times with water and three times with brine. The ethyl acetate layer was dried over Na2SO4, filtered and evaporated to an oil. Purification by radial chromatography (2-8%methanol-chloroform gradient with 0.25% NH40H) gave 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester (72 mg, 32%) as an oil.
Workup
- washwashed three times with water and three times with brine
- dry with materialThe ethyl acetate layer was dried over Na2SO4
- filtrationfiltered
- customevaporated to an oil
- customPurification by radial chromatography (2-8%methanol-chloroform gradient with 0.25% NH40H)
Sources & evidence
- ORD record
- ord-30293e2d83764967a00c2d6f3332a52f
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06693123B2
Reaction notes
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