Triethylamine → tert-Butyl (S)-(1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)carbamate
Reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.[C:12]([NH:19][C@H:20]([C:28]([OH:30])=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:2][N:3]([CH3:4])[C:28](=[O:30])[C@H:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:19][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of dimethylamine hydrochloride (1.45 g, 17.8 mmol) in DMF (46 mL) was cooled to −10° C. and triethylamine (2.7 mL, 19.4 mmol) was added. N-Boc-L-phenylalanine (4.59 g, 17.3 mmol, Aldrich) and HOBt (3.49 g, 26 mmol) were then added and the reaction stirred for 5 min before addition of EDCI (3.33 g, 17.4 mmol). The reaction mixture was left to stir for 16 h then diluted with ethyl acetate (400 mL), washed sequentially with aqueous sodium hydroxide solution (2M, 2×100 mL), hydrochloric acid (2N, 2×100 mL), brine (250 mL) and then dried (MgSO4). Evaporation in vacuo gave the title compound as a pale yellow oil. δH (CDCl3): 1.41 (9H, s), 2.61, 2.85 (6H, 2s), 2.91–2.99 (2H, m), 4.83 (1H, m), 5.40 (1H, br d), 7.18–7.29 (5H, m).
Workup
- waitThe reaction mixture was left
- washwashed sequentially with aqueous sodium hydroxide solution (2M, 2×100 mL), hydrochloric acid (2N, 2×100 mL), brine (250 mL)
- dry with materialdried (MgSO4)
- customEvaporation in vacuo
Sources & evidence
- ORD record
- ord-fabdcd7c45884d58ae3ccd93b51bdc8f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405210B2
Reaction notes
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