Dimethylformamide → Fmoc-leucine

HRID 396114

Reaction equation

HRID 396114 reaction equation
[C:1]([N:18](CC(C)C)[CH2:19][C:20]([OH:22])=[O:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].S(Cl)(Cl)=O.CN(C=O)C>C(Cl)Cl>[NH:18]([C:1]([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2])[C@H:19]([C:20]([OH:22])=[O:21])[CH2:4][CH:5]([CH3:17])[CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11727923Glycine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-(2-methylpropyl)-

Product 1

HCID 1549133Fmoc-leucine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

FMOC-Leu*-Cl was prepared by dissolving FMOC-N-isobutylglycine (150 mg, 0.42 mmol) in CH2Cl2 (2.8 mL), and adding thionyl chloride (309 μL, 4.2 mmol) and 3 μL DMF (0.04 mmol). The reaction mixture was stirred for 5 hours and concentrated in vacuo, repeatedly dissolving in CH2Cl2 (3××) to provide FMOC-Leu*-Cl as a colorless oil (146 mg, 92%): IR (cm−1) −1804, 1720, 1715. FMOC-Phe*-Cl was similarly prepared.

Workup

  1. customFMOC-Leu*-Cl was prepared
  2. concentrationconcentrated in vacuo
  3. dissolutionrepeatedly dissolving in CH2Cl2 (3××)

Sources & evidence

ORD record
ord-6034ad8ef5ff4f3dae7ffeb683697265
Source dataset
uspto-grants-2003_08
Patent number
US06608026B1

Linked notes

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