Indole → HCID 131723561, compound

HRID 992406Notes

Reaction equation

HRID 992406 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:30]([N-:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:31]([CH3:33])[CH3:32].CSC.C(S)CS.N1C2C(=CC=CC=2)C=C1.N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C@@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:30]([N-:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:31]([CH3:33])[CH3:32]

Participants

8

Reactant 6

HCID 798IndoleHCID 1068Dimethyl SulfideHCID 6305L-TryptophanHCID 6422Trifluoroacetic acidHCID 109021,2-EthanedithiolHCID 131723562HCID 131723562, compound

Product 1

HCID 131723561HCID 131723561, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-DTrp-DPro-diisobutylamide was dissolved in 25 ml of CH2Cl2, 1 ml of methylsulfide and 0.5 ml of 1,2-ethanedithiol was added as scavenger in suppressing the indole alkylation of tryptophane. 10 ml of trifluoracetic acid was added dropwise while being stirred. The reaction mixture was stirred for 30 min. Volatiles were removed under vacuum and the residue was dissolved in 30 ml of CH2Cl2 and washed with 10 ml saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous sodium sulfate and filtered and the solvents were removed in vacuum. The residue was further purified by column chromatography (SiO2, CHCl2/MeOH, 85:15) to afford 0.55 mmol (78.5%) of compound (2) which was characterized by TLC and mass spectra, M+=411.5.

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. customVolatiles were removed under vacuum
  3. dissolutionthe residue was dissolved in 30 ml of CH2Cl2
  4. washwashed with 10 ml saturated NaHCO3 aqueous solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed in vacuum
  8. customThe residue was further purified by column chromatography (SiO2, CHCl2/MeOH, 85:15)

Sources & evidence

ORD record
ord-2f0dc489546240478d0541929f0723d2
Source dataset
uspto-grants-2002_10
Patent number
US06468974B1

Reaction notes

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