Methylamine → HCID 15045057, compound

HRID 1089836Notes

Reaction equation

HRID 1089836 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24](O)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:27][NH2:28]>C1COCC1.ClCCl>[CH3:27][NH:28][C:24](=[O:25])[C@H:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 1549133Fmoc-leucine

Product 1

HCID 15045057HCID 15045057, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride (3.5 g, 10 mmol) in 50 mL of THF was charged with solution of methylamine (0.62 g, 20 mmol) in 50 mL of dichloromethane, at room temperature. The reaction mixture was stirred for 30 min. The solvents were removed and the residue was dissolved in 100 mL of ethyl acetate. The solution was washed with aqueous solution of 10% potassium carbonate, water, brine, dried over magnesium sulfate and evaporated. Recrystallization of the product from ethyl acetate/hexane mixture afforded 1.67g (46.6%) of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine methylamide, mp 173°-174° C.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in 100 mL of ethyl acetate
  3. washThe solution was washed with aqueous solution of 10% potassium carbonate, water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customRecrystallization of the product from ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-91af67c60f074a42bdb6f781e0b2b110
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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