Triethylamine → HCID 22869005, compound

HRID 234091Notes

Reaction equation

HRID 234091 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 22869005HCID 22869005, compoundYield 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 ml) 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-1dd953086b074d138b3cc83a4f17b338
Source dataset
uspto-grants-1997_01
Patent number
US05594106

Reaction notes

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