Water → Leucyl-leucine-methyl ester

HRID 2205268Notes

Reaction equation

HRID 2205268 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=C[C:11]=2[N:10]=N1.[CH3:28]CN(CC)CC.N[C@H:36]([C:41]([O:43][CH3:44])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39].Cl.[OH2:46]>C(Cl)Cl>[NH2:8][C@H:12]([C:11]([NH:10][C@H:36]([C:41]([O:43][CH3:44])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:46])[CH2:13][CH:14]([CH3:15])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 7016877Leucyl-leucine-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 3 (10 mmol), BOP (10 mmol) and Et3N (13 mmol) in CH2Cl2 (20.0 mL) was added H2N-Leu-OMe HCl (10 mmol) and stirred at RT for 12 hrs. The reaction mixture was diluted with water, organic layer was separated and solvent was evaporated in vacuo. The crude product was purified by flash chromatography (20-40% EtOAc/Hexanes) afforded EPA-Leu-Leu-OMe, compound 4 intermediate (6.5 mmol) as light yellow syrup. The obtained intermediate was hydrolyzed with 1N NaOH and subsequent quenching with dil HCl, and extracted with EtOAc (2×10 mL) provided ((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl)-L-leucyl-L-leucinate, compound 4 as yellow syrup.

Workup

  1. customwas separated
  2. customsolvent was evaporated in vacuo
  3. customThe crude product was purified by flash chromatography (20-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6f910da860384b1aa3917e7d422b0c20
Source dataset
uspto-grants-2016_06
Patent number
US09371276B1

Reaction notes

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