Triethylamine → HCID 54526617, compound

HRID 234088Notes

Reaction equation

HRID 234088 reaction equation
Cl.[C:2]([NH:12][CH2:13][CH2:14][NH2:15])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:16]([NH:23][C@H:24]([C:26](O)=[O:27])[CH3:25])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(N(CC)CC)C>CN(C)C=O>[CH2:5]([O:4][C:2]([NH:12][CH2:13][CH2:14][NH:15][C:26](=[O:27])[C@H:24]([CH3:25])[NH:23][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochloride

Product 1

HCID 54526617HCID 54526617, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 10.0 g (0.043 mol) of (1f) and 10.3 g (0.036 mol) of N-BOC-L-alanine, N-hydroxysuccinimide ester in anhydrous N,N-dimethylformamide (50 ml) was cooled with an ice bath. To this was added 7.6 ml (0.054 mol) of triethylamine in anhydrous N,N-dimethylformamide (20 ml) over a period of 30 minutes. The reaction was stirred at ca. 5° C. for 1 hour, then at room temperature for 1 hour. The N,N-dimethylformamide was removed in vacuo and the resulting residue was dissolved in 300 ml of ethyl acetate. The solution was washed with 1M HCl (3×100 ml), water (100 ml), saturated sodium bicarbonate solution (3×100 ml) and finally, with brine (100 ml). After drying over anhydrous magnesium sulfate, the solution was filtered and concentrated in vacuo to give 12.4 g (94% yield) of N-BOC-L-alanine, 2-(benzyloxycarbonylamino)ethyl amide (1g) as a white solid. TLC: Rf 0.67 (chloroform-isopropanol 9:1); 1H NMR(CDCl3) δ 1.27(d, 3H), 1.40(s, 9H), 3.32(m, 4H), 4.15(m, 1H), 5.06(s, 2H), 5.51(d, 1H), 5.90(m, 1H), 7.19(m, 1H), 7.31(bs, 5H); 13C NMR (CDCl3) δ 18.5, 28.2, 39.6, 40.5, 50.1, 66.5, 79.8, 127.9, 128.3, 136.3, 155.4, 156.9, 173.7.

Workup

  1. waitat room temperature for 1 hour
  2. customThe N,N-dimethylformamide was removed in vacuo
  3. dissolutionthe resulting residue was dissolved in 300 ml of ethyl acetate
  4. washThe solution was washed with 1M HCl (3×100 ml), water (100 ml), saturated sodium bicarbonate solution (3×100 ml)
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationthe solution was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5b6d4061b144c98830ecba22a48cc76
Source dataset
uspto-grants-1997_01
Patent number
US05594106

Reaction notes

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