Acetonitrile → Leu-Leu-OBzl

HRID 537625Notes

Reaction equation

HRID 537625 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[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]([NH:9][C@H:10]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8021Diethylamine2×HCID 102027077Fmoc-Leu-Leu-OBzl

Product 1

HCID 54422096Leu-Leu-OBzl

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fmoc-Leu-Leu-OBzl (2-MeO-4-OC12OC22) (1.02 g) was dissolved in chloroform (10 mL), and diethylamine (1.94 mL, 18.7 mmol) was added dropwise under ice-cooling. The mixture was warmed to room temperature, acetonitrile (5 mL) was added, and the mixture was stirred for 2.5 hr. Diethylamine (970 μL, 9.35 mmol) was added, and the mixture was further stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was precipitated with acetonitrile (10 mL) to give Leu-Leu-OBzl (2-MeO-4-OC12OC22) as wet crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was precipitated with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-2080b6d4e813403295442c951dc3af99
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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