1,2-Dichloroethane → Ethyl 3-(5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)pentanoylamino)-3(S)-(quinolin-3-yl)-propionate
Reaction equation
Cl.[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O.Cl.Cl.[CH2:21]([O:23][C:24](=[O:38])[CH2:25][CH:26]([NH2:37])[C:27]1[CH:28]=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:22].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:37][C@H:26]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:38])=[O:18]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1-6 (200 mg, 0.74 mmol), 5-7 (202 mg, 0.74 mmol), NMM (366 mL, 3.33 mmol), HOBT (130 mg, 0.96 mmol) and EDC (184 mg, 0.96 mmol) in 2 mL DMF was stirred overnight. After diluting with EtOAc (100 mL), the mixture was washed with sat. NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated, and chromatographed on silica (10% EtOH/EtOAc) providing 5-8 as a colorless glass.
Workup
- washthe mixture was washed with sat. NaHCO3, water, and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica (10% EtOH/EtOAc)
Sources & evidence
- ORD record
- ord-974ef8a495a441eab9ac3f8bffb90629
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297249B1
Reaction notes
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