Reaction equation
[N:1]1([CH2:11][CH2:12][C:13]([OH:15])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.C1(=O)N(OC(N(C)C)=[N+](C)C)C(=O)CC1.C(N(CC)C(C)C)(C)C.[NH2:45][CH:46]([CH2:48][CH2:49][CH2:50][N:51]([CH2:54][CH3:55])[CH2:52][CH3:53])[CH3:47]>CN(C=O)C.[Cl-].[Na+].O>[CH2:54]([N:51]([CH2:52][CH3:53])[CH2:50][CH2:49][CH2:48][CH:46]([NH:45][C:13](=[O:15])[CH2:12][CH2:11][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH3:47])[CH3:55]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of Compound 4 (1.9 g, 9.3 mmol) in DMF (35 mL), 2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate (3.4 g, 11.2 mmol) and N,N-diisopropyl ethylamine (3.4 mL, 19.5 mmol) were added. Combined mixture was stirred at room temperature for 30 mins and then a solution of 2-amino-5-diethylaminopentane (2.2 g, 13.9 mmol) in DMF (5 mL) was added. After stirring the mixture for additional 1 hour, it was poured in brine (100 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with brine (3×100 mL) and dried over MgSO4. The solvent was removed under reduced pressure to provide Compound 5 as a dark yellow viscous liquid (2.64 g, 82.5%). This product was used without further purification. The structure of Compound 5 is given below:
Workup
- stirringAfter stirring the mixture for additional 1 hour
- extractionextracted with ethyl acetate (2×75 mL)
- washThe combined organic layers were washed with brine (3×100 mL)
- dry with materialdried over MgSO4
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-0b91d426239f4f24b4a4dc69d856f2e5
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09250249B2
Linked notes
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