Dimethylformamide → HCID 22137605, compound
Reaction equation
[C:1]([O:5][C:6](N1CCC(C(O)=O)CC1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.C1C=CC2N([OH:33])N=NC=2C=1.[CH3:34][CH2:35][N:36]=[C:37]=NCCCN(C)C.CN([CH:48]=[O:49])C>>[C:1]([O:5][C:6]([C:34]1([C:35]([N:36]([O:49][CH3:48])[CH3:37])=[O:33])[CH2:21][CH2:20][NH:19][CH2:22][CH2:23]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
To a stirring suspension of t-Boc-isonipecotic acid (19) (2.34 g, 10.2 mmol) and the Weinreb amine (1.5 g, 15 mmol) in DMF (50 mL), was added triethylamine (2.8 mL, 20 mmol) at room temperature. After stirring for 10 min, HOBt (1.62 g, 12 mmol) was added, followed by EDCI (2.3 g, 12 mmol). The resulting solution was stirred overnight and concentrated. The residue was taken up in 1 N HCl (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with sat NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated to obtain a colorless oil (20) (2.79 g, >100%). 1H NMR (500 MHz, CDCL3) δ 4.14 (m, 2H), 3.71 (s, 3H), 3.19 (s, 3H), 2.78 (m, 3H), 1.68 (m, 4H), 1.46 (s, 9H); MS (ESI+) m/z 217.72 (M+H+-isobutylene).
Workup
- stirringThe resulting solution was stirred overnight
- concentrationconcentrated
- extractionextracted with EtOAc (3×100 mL)
- washThe combined organic extracts were washed with sat NaHCO3 (50 mL), brine (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-576de55be6ae488aba21d6d011de3e0c
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053214B2
Reaction notes
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