Dicyclohexylcarbodiimide → HCID 18597345, compound

HRID 1980826Notes

Reaction equation

HRID 1980826 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:21]([NH:17][C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-Valine

Product 1

HCID 18597345HCID 18597345, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 butyloxy-carbonyl-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, 3xCH3); 1.3 (8H,m,(CH2)4); 1.45 (9H,s, (CH3)3C); 2.1 (1H, m,CH(CH3)2); 3.3 (2H,m, NHCH 2); 3.9 (1H,dd, J=8 Hz and 5 Hz., α--CH); 5.2 (1H,d, J=8 Hz, CONH) and 6.26 (1H,m,NH).

Workup

  1. filtrationThe solution was filtered
  2. washthe organic phase washed with aqueous sodium hydrogen carbonate, aqueous citric acid (1M) and water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93867f289c8742f3ba4ad0a79cc26952
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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