Triethylamine → N-(tert-Butoxycarbonyl)-L-tryptophyl-L-methioninamide

HRID 371354Notes

Reaction equation

HRID 371354 reaction equation
[NH2:1][C@H:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].C(N(CC)CC)C.[NH:17]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:18]([C:29](ON1C(=O)CCC1=O)=[O:30])[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1>CN(C=O)C>[NH:17]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:18]([C:29]([NH:1][C@H:2]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:30])[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98767tert-Butyl (S)-(2-((2,5-dioxo-1-pyrrolidinyl)oxy)-1-(1H-indol-3-ylmethyl)-2-oxoethyl)carbamateHCID 1464802-Amino-4-(methylsulfanyl)butanimidic acid

Product 1

HCID 13306577N-(tert-Butoxycarbonyl)-L-tryptophyl-L-methioninamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.78 g (0.039 mole) of H-Met-NH2 was dissolved in 50 ml of DMF, then 5.46 ml of triethylamine and further 18.70 g (0.047 mole) of Boc-Trp-OSu were added under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and extracted with ethyl acetate. The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series. The resulting organic layer was dried over anhydrous sodium sulfate, distilled in vacuo to remove the solvent, and solidified with hexane. The solid was recrystallized from ethyl acetate-hexane, giving 12.45 g of Boc-Trp-Met-NH2 ; yield 73.5%, m.p. 155°-157° C.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series
  5. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  6. distillationdistilled in vacuo
  7. customto remove the solvent
  8. customThe solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b6b89f651926450dbad031efbd8b183c
Source dataset
uspto-grants-1985_07
Patent number
US04530836

Reaction notes

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