Triethylamine → HCID 54049046, compound
Reaction equation
[O:1]=[C:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.Cl.[CH3:17][O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH2:21].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH:21][C:8](=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]Participants
Conditions
- Temperature
- 0 °C
Procedure
7-oxododecanoic acid (1000 mg, 4.67 mmoles) and L-alanine methyl ester hydrochloride (656 mg, 4.7 mmoles) were dissolved in N,N-dimethylformamide (5 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (1300 mg, 4.72 mmoles) and triethylamine (950 mg, 0.95 mmoles) were added thereto. The reaction mixture was stirred for 1 hour on an ice bath and for 24 hours at room temperature. The resulting suspension was diluted with ethyl acetate (30 ml) and washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the compound was precipitated from n-hexane/diethyl ether.
Workup
- washwashed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml)
- dry with materialThe organic phase was dried with MgSO4
- filtrationfiltered
- customthe filtrate was evaporated
- customthe compound was precipitated from n-hexane/diethyl ether
Sources & evidence
- ORD record
- ord-0bdaefa3d58a4a898a36f719162b9449
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05514654
Reaction notes
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