Dimethyl Sulfide → HCID 131723565, compound

HRID 1297201Notes

Reaction equation

HRID 1297201 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C:2]([C:5]([NH:7][C@@H:8]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])([CH3:4])[CH3:3].[CH2:36]([N-:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH:37]([CH3:39])[CH3:38].CSC.C(S)CS.N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]([C:5]([NH:7][C@@H:8]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])([CH3:3])[CH3:4].[CH2:36]([N-:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH:37]([CH3:39])[CH3:38]

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 6305L-TryptophanHCID 6422Trifluoroacetic acidHCID 109021,2-EthanedithiolHCID 131723563HCID 131723563, compound2×

Product 1

HCID 131723565HCID 131723565, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-Aib-DTrp-DPro-diisobutylamide was dissolved in 30 ml of CH2Cl2, 1 ml of methylsulfide and 0.5 ml of 1,2-ethanedithiol were added as scavengers to suppress the indole alkylation of tryptophan. 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 removed and the aqueous layer was extracted with CH2Cl2 (3×10 ml). 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, CHCl/MeOH, 85:15) to afford 0.43 mmol (86.2%) of compound (YL-156) which was characterized by TLC and mass spectra M+=497.6.

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. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 ml)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed in vacuum
  10. customThe residue was further purified by column chromatography (SiO2, CHCl/MeOH, 85:15)

Sources & evidence

ORD record
ord-bfc73910678c4c369c2e21727569262b
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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