Acetonitrile → Benzyl L-leucinate

HRID 1502553Notes

Reaction equation

HRID 1502553 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(NCC)C.C(#N)C>C(Cl)(Cl)Cl>[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8021DiethylamineHCID 11048505HCID 11048505, compound

Product 1

HCID 6451313Benzyl L-leucinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The crude crystals (942 mg) of Fmoc-Leu-OBzl (2-MeO-4-OC12OC22) were dissolved in chloroform (9 mL), and diethylamine (1.99 mL, 19.2 mmol) was added dropwise under ice-cooling. The mixture was warmed to room temperature, acetonitrile (4.5 mL) was added, and the mixture was stirred for 3.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was precipitated with acetonitrile (10 mL) to give Leu-OBzl (2-MeO-4-OC12OC22) as wet crystals.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was precipitated with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-a41cee151dbb4263afb6b731b694f792
Source dataset
uspto-grants-2015_12
Patent number
US09206230B2

Reaction notes

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