1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(2,2-dimethoxyethyl)-2-(4-methylbenzenesulfonamido)pent-4-ynamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:38][O:39][CH:40]([O:43][CH3:44])[CH2:41][NH2:42].CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:38][O:39][CH:40]([O:43][CH3:44])[CH2:41][NH:42][C:13](=[O:15])[C@H:12]([NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])[CH2:16][C:17]#[CH:18]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid (11.0 g, 41.2 mmol), HOBt (6.67 g, 49.4 mmol), iPr2NEt (6.40 g, 49.4 mmol), (2,2-dimethoxyethyl)amine (8.70 g, 82.33 mmol), and EDCI (9.5 g, 49 mmol) in DMF (100 mL) was stirred for 24 h at RT. The reaction mixture was concentrated, taken up in H2O, and extracted with EtOAc (3×). The organic extracts were dried over MgSO4 and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3): δ 2.15 (s, 1H), 2.43 (m, 1H), 2.51 (s, 3H), 2.88 (m, 1H), 2.94 (s, 3H), 2.96 (s, 3H), 3.37 (m, 3H), 3.85 (m, 1H), 4.33 (m, 1H), 6.78 (s, 1H), 7.33 (d, 8.0 Hz, 2H), 7.76 (d, 8.0 Hz, 2H), 8.01 (s, 1H).
Workup
- concentrationThe reaction mixture was concentrated
- extractionextracted with EtOAc (3×)
- dry with materialThe organic extracts were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6772d50de44a48c4b0ef55145c3ce161
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612060B2
Reaction notes
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