Triethylamine → Nalpha-BOC-Nepsilon-CBZ-L-lysyl-L-alanine amide

HRID 1779913Notes

Reaction equation

HRID 1779913 reaction equation
[N+](C1C=CC(O[C:11](=[O:36])[C@H:12]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=CC=1)([O-])=O.Cl.[NH2:38][C@H:39]([C:41]([NH2:43])=[O:42])[CH3:40].C(N(CC)CC)C>CN(C)C=O>[C:14]([NH:13][C@H:12]([C:11]([NH:38][C@H:39]([C:41]([NH2:43])=[O:42])[CH3:40])=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 140194182389-46-0

Product 1

HCID 22869005Nalpha-BOC-Nepsilon-CBZ-L-lysyl-L-alanine amideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Referring to Scheme 6, a solution of 5.0 g (0.010 mol) of Nα-BOC-Nε-CBZ-L-lysine p-nitrophenyl ester and 1.5 g (0.012 mol) of L-alanine amide hydrochloride and 1.67 ml (0.012 mol) of triethylamine in anhydrous N,N-dimethylformamide (50 mi) was stirred at room temperature for 16 hours before the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate (200 ml) and washed with 3M NaOH (3×100 ml), water (3×100 ml), 1M HCl (2×100 ml) and finally with brine (100 ml). After drying over anhydrous sodium sulfate, the solution was filtered and concentrated in vacuo to give 4.3 g (96% yield) of Nα-BOC-Nε-CBZ-L-lysyl-L-alanine amide (6a) as a white solid. TLC: Rf 0.32 (chloroform-isopropanol 9:1); 1H NMR (d6 -DMSO) δ 1.20(d,3H), 1.35(bm, 6H), 1.37(s,9H), 2.97(m,2H), 3.86(m,1H), 4.21(m,1H), 5.00(s,2H), 6.95(d,1H), 7.06(s, 1H), 7.24(t,1H), 7.34(m,6H), 7.78(d,1H); 13C NMR (d6 -DMSO) δ 18.6, 22.8, 28.2, 29.2, 31.4, 40.1, 47.8, 54.5, 65.2, 78.2, 127.8, 128.4, 137.3, 155.5, 156.1, 171.7, 174.2.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (200 ml)
  3. washwashed with 3M NaOH (3×100 ml), water (3×100 ml), 1M HCl (2×100 ml) and finally with brine (100 ml)
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationthe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3187f1075f8240f69c498fd740e7cf14
Source dataset
uspto-grants-1997_05
Patent number
US05629285

Reaction notes

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