1,1'-Carbonyldiimidazole → (S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester
Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.N12CCCN=C1CCCCC2.Cl.[CH3:37][O:38][C:39](=[O:46])[C@@H:40]([NH2:45])[CH2:41][CH2:42][CH2:43][CH3:44]>N1C=CC=CC=1.CCOC(C)=O>[CH3:37][O:38][C:39](=[O:46])[C@@H:40]([NH:45][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[NH2:1])[CH2:41][CH2:42][CH2:43][CH3:44]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-amino-4-methoxy-benzoic acid (1.0 g, 5.98 mmol) and 1,1′-carbonyldiimidazole (980 mg, 6.04 mmol) in pyridine (5 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.9 mL, 6.02 mmol). The mixture is stirred at room temperature for 2 hours follows by the addition of (S)-2-amino-hexanoic acid methyl ester hydrochloride (1.1 g, 6.06 mmol). The reaction mixture is stirred at room temperature for 16 hours and diluted with EtOAc (100 mL), the solution is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, and is concentrated. The resulting residue is purified by flash chromatography with 60% EtOAc in hexanes as the eluent to afford (S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester (1.03 g, 59%).
Workup
- stirringThe reaction mixture is stirred at room temperature for 16 hours
- washthe solution is washed with H2O (50 mL×3)
- dry with materialThe organic layer is dried over sodium sulfate
- concentrationis concentrated
- customThe resulting residue is purified by flash chromatography with 60% EtOAc in hexanes as the eluent
Sources & evidence
- ORD record
- ord-8bfc118369f54071991b23aa6fcb154a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377949B2
Reaction notes
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