[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:12]([CH:15]([CH2:19][C:20]#[CH:21])[C:16](O)=O)[C:13]#[CH:14].CN([C:25]([O:29]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][NH:11][C:25](=[O:29])[CH2:16][CH:15]([CH2:19][C:20]#[CH:21])[CH2:12][C:13]#[CH:14])([CH3:5])([CH3:6])[CH3:7]
N-boc-ethylenediamine (18.3 gm, 0.1143 mol) in 50 ml of CH3CN was added slowly via an addition funnel to a stirred solution containing dipropargylacetic acid (15.56 gm, 0.1143 mol), TBTU (36.74 gm, 0.114 mol) and DIPEA (29.6 gm, 0.229 mol) in 300 ml of CH3CN at 0 C. Precipitation occurred. The ice bath was removed and the product was stirred at ambient temperature overnight (16 hours). The reaction was now totally homogeneous. The solution was concentrated in vacuo and the residue was diluted with 800 ml of water. The resulting solids were filtered, washed copiously with water, and vacuum dried to give 14.3 gm of crude product. Re-crystallization (2×) from DCM, filtration and washing with hexanes affords the product (9.85 gm, 31% yield, 98% purity by HPLC (214 nm)).
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