Diisopropylethylamine → HCID 86583707, compound

HRID 2183070Notes

Reaction equation

HRID 2183070 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4](=[O:13])[CH2:5][C@@H:6]([CH2:10][CH:11]=[CH2:12])[C:7]([OH:9])=O.O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:28]([O:30][C:31](=[O:36])[C@H:32]([CH2:34][OH:35])[NH2:33])[CH3:29].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:14][C:2]([CH3:1])([CH3:15])[CH2:3][C:4](=[O:13])[CH2:5][C@@H:6]([CH2:10][CH:11]=[CH2:12])[C:7]([NH:33][C@@H:32]([CH2:34][OH:35])[C:31]([O:30][CH2:28][CH3:29])=[O:36])=[O:9]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724185L-Serine, ethyl ester, hydrochloride (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 86583708HCID 86583708, compound

Product 1

HCID 86583707HCID 86583707, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution (2R)-2-(4,4-dimethyl-2-oxopentyl)-4-pentenoic acid (Preparation 112) (15.91 g, 74.3 mmol), 1-hydroxybenzotriazole hydrate (11.00 g, 81.4 mmol), L-serine ethylester hydrochloride (13.84 g, 81.6 mmol) and N,N-diisopropylethylamine (27 ml, 156.0 mmol) in dichloromethane (280 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15.67 g, 81.7 mmol) and stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was diluted with dichloromethane and washed with water, aqueous citric acid (2M), saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulphate and filtered. The solvent was removed under reduced pressure to afford the title compound as a yellow oil (23.8 g).

Workup

  1. washwashed with water, aqueous citric acid (2M), saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3de9c91ac09243fca525f7fdd28a6bb9
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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