Triethylamine → HCID 131731438, compound

HRID 1755196Notes

Reaction equation

HRID 1755196 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH3:7])[CH3:6].[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22][C@H:23]([NH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[C:24](O)=[O:25])=[CH:18][CH:17]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH2:31]([O:30][C:28]([NH:27][C@H:23]([C:24]([NH:2][CH2:3][CH:4]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:5]([CH3:7])[CH3:6])=[O:25])[CH2:22][C:19]1[CH:18]=[CH:17][CH:16]=[CH:21][CH:20]=1)=[O:29])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 757711-HydroxybenzotriazoleHCID 87093237HCID 87093237, compound

Product 1

HCID 131731438HCID 131731438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (2S)-1-amino-2-tert-butyloxycarbonylamino-3-methylbutane hydrochloride was obtained from tert-butyloxycarbonyl-L-valinol in accordance with the literature procedures (Mattingly, P. G., Synthesis, 1990, 1990, 366-368. Desired Boc-protected alcohol was obtained from Boc-L-valine, in accordance with the literature procedure (Juszczyk, P. et al., Letters In Peptide Science. 2003, 10, 79-82). The solution of (2S)-1-amino-2-tert-butyloxycarbonylamino-3-methylbutane hydrochloride (0.50 g, 2.096 mmol), Z-L-phenylalanine (0.659 g, 2.20 mmol), triethylamine (611 μl, 4.4 mmol) and HOBt (0.297 g. 2.20 mmol) in 10 ml of DMF was cooled on ice bath and DCC (0.498 g, 2.42 mmol) was added in small portions, during 0.5 h. The stirring was continued during 1 hour, next the reaction mixture was left in room temperature overnight. The precipitated DCU was filtered off, washed with DMF (2×3 ml) and the combined filtrates were evaporated under reduced pressure. The solid residue was dissolved in ethyl acetate (200 ml) and the solution was washed with 1 M hydrochloric acid (3×70 ml),

Workup

  1. waitwas left in room temperature overnight
  2. filtrationThe precipitated DCU was filtered off
  3. washwashed with DMF (2×3 ml)
  4. customthe combined filtrates were evaporated under reduced pressure
  5. dissolutionThe solid residue was dissolved in ethyl acetate (200 ml)
  6. washthe solution was washed with 1 M hydrochloric acid (3×70 ml)

Sources & evidence

ORD record
ord-083d3db3ff03485c82f08979fe0d1e39
Source dataset
uspto-grants-2015_10
Patent number
US09169289B2

Reaction notes

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