Dicyclohexylcarbodiimide → HCID 18597345, compound

Participants

Reaction Steps

Tertiarybutyloxycarbonyl-L-valine (25 g) in dichloromethane (200 ml) was treated with 1-hydroxybenzotriazole (15.5 g) hexylamine (11.6 g) and DCC (26 g) at room temperature for 2 days. The solution was filtered and the organic phase washed with aqueous sodium hydrogen carbonate, aqueous citric acid (1M) and water, dried over sodium sulphate and concentrated in vacuo to afford tertiary butyloxycarbonyl-L-valine N-hexylamide (28 g) which crystallised from methanol-water as needles; m.p. 74°-76° C.; (Found: C,63.8; H,10.6; N,9.4. C16H32N2O3 requires C,64.0; H,10.7; N,9.32%); νmax (Nujol): 3280 and 1630 cm-1 ; δ(CDCl3) 0.8-1 (9H,m, 3×CH3); 1.3 (8H,m,(CH2)4); 1.45 (9H,s, (CH3)3C); 2.1 (1H,m,CH(CH3)2); 3.3 (2H,m, NHCH2 ); 3.9 (1H,dd, J=8 Hz and 5 Hz., α-CH); 5.2 (1H,d, J=8Hz, CONH) and 6.26 (1H,m,NH).

Provenance & Evidence