Triethylamine → HCID 88141407, compound
Reaction equation
CC(C)([O:4][C:5]([NH:7][C@H:8]([C:13]([NH:15][CH:16]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:17]([P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20])[OH:18])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])C.CC(C[C@H](NC(O[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O)C(O)=O)C.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:46]1([CH2:45][O:4][C:5]([NH:7][C@H:8]([C:13]([NH:15][C@@H:16]([CH2:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[CH:17]([P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20])[OH:18])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The title E compound of Example 1 (749.3 mg, 2.5 mmol) was added to a solution of N-α-CBZ-L-Leucine (548.5 mg, 2.07 mmol) in dimethylformamide (10 mL) and cooled to 0° C. Hydroxybenzotriazole hydrate (348.3 mg, 2.27 mmol), triethylamine (432.7 μl, 3.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (436.4 mg, 2.27 mmol) were added sequentially. After 16 hours at 25° C., pH 4.01 buffer solution was added and the reaction mixture was stirred for 10 minutes. The resulting precipitate was filtered, washed sequentially with pH 4.01 buffer (3×50 mL) and water (3×50 mL) and dried over sodium sulfate yielding 804 mg of crude material. Flash chromatographic purification afforded 546.4 mg of the title compound as a white solid, m.p. 151° C., [α]D -56.2° (c=1.04, CH3OH).
Workup
- filtrationThe resulting precipitate was filtered
- washwashed sequentially with pH 4.01 buffer (3×50 mL) and water (3×50 mL)
- dry with materialdried over sodium sulfate yielding 804 mg of crude material
- customFlash chromatographic purification
Sources & evidence
- ORD record
- ord-398f0f9202694bddb2620cec5b1b91de
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05217958
Reaction notes
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